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From $199 per night (USD)
VRBO
Cottage in the Woods on Picturesque Island
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Nestled in the woods on picturesque Peaks Island, this delightful cabin 'Sequester' offers guests a tranquil escape. Wit ...
From $199 per night (USD)
VRBO
From $1037 per night (USD)
Expedia
Spacious 7-bedroom house in marvelous Portland with AC, WiFi
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Discover this charming 7-bedroom gem in Portland. This lovely house boasts heating, AC, and WiFi for your comfort. With ...
From $1037 per night (USD)
Expedia
From $185 per night (USD)
VRBO
Studio Unit Walkable Everywhere
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Recently updated clean & no frills 1st floor unit in a 3 floor brick building walkable to all in-town Portland hot spots ...
From $185 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Private Entrance Residential Portland
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A great, simple1 bedroom apartment in a 3 unit building located in quiet suburban neighborhood of outer Portland. A 10-1 ...
From $185 per night (USD)
Expedia
From $755 per night (USD)
VRBO
Amazing West End apartment walkable to downtown and the waterfront.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Nestled in Portland’s charming West End, this spacious and bright 2 BR offers upscale amenities and a refined sense of c ...
From $755 per night (USD)
VRBO
From $354 per night (USD)
Expedia
2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Get ready to relax in this 2-bedroom apartment in Portland. The space features 2 cozy queen beds, WiFi, heating, and AC. ...
From $354 per night (USD)
Expedia
From $1788 per night (USD)
VRBO
Downtown Portland Retreat | 3 Units | Near Breweries & Scenic Harbor!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $1788 per night (USD)
VRBO
From $1191 per night (USD)
Expedia
2 Family Ready Rooms | Pet-Friendly Stay, Walking Distance to Museum of Art
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $1191 per night (USD)
Expedia
From $1191 per night (USD)
VRBO
Pet-Friendly Stay | 2 Units | Close to Victoria Mansion & Lighthouse!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $1191 per night (USD)
VRBO
From $596 per night (USD)
Expedia
Stylish Stay | Savor Seafood & Explore Portland’s History!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $596 per night (USD)
Expedia
From $596 per night (USD)
VRBO
Spacious Downtown Waterfront Unit | Pets Are Welcome | Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $596 per night (USD)
VRBO
From $2384 per night (USD)
Expedia
4 Cozy Units | Downtown Stay, Waterfront & Near Vibrant Old Port District
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $2384 per night (USD)
Expedia
From $564 per night (USD)
VRBO
Relaxing Couple Pet-Friendly Stay | Seafood & Portland Attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $564 per night (USD)
VRBO
From $198 per night (USD)
Expedia
Marvelous 2-bedroom apartment in Portland
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Portland is waiting for you at this delightful 2-bedroom apartment. With a queen bed, a full bed, and a cozy living room ...
From $198 per night (USD)
Expedia
From $387 per night (USD)
VRBO
Near Portland Trails: Walkable Apartment w/ Deck
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Open Layout | In-Unit Laundry | Half-Mi to Restaurant & Market Discover Portland, ME, like a local at this 1-bedroom, 1 ...
From $387 per night (USD)
VRBO
From $440 per night (USD)
Expedia
Beautiful Unit in Serene Countryside Setting Near Wineries – Onsite Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore Maine's coastal charm with nearby wineries and breweries, or stroll through Old Port for the perfect blend of se ...
From $440 per night (USD)
Expedia
From $1782 per night (USD)
VRBO
6BR Sleeps 16 w/ Balcony 10 mins to Downtown
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
Bringing everyone together? This 6BR, 4.5BA setup combines two private apartments in the same building—perfect for group ...
From $1782 per night (USD)
VRBO
From $637 per night (USD)
Expedia
State of Charm | Historic West End Haven
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2 bedroom condo is in a landmark home situated on Portland's desirable peninsula. Enjoy being within walking distan ...
From $637 per night (USD)
Expedia
From $705 per night (USD)
VRBO
Lofty Ambition | Stunning West End Rooftop Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into this dazzling retreat perched atop Portland’s historic West End! Bathed in sunlight and bursting with characte ...
From $705 per night (USD)
VRBO
Click For Pricing
Expedia
Historic Charm at 236 - Elegant West End Retreat
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Stay in the heart of Portland’s historic West End at an iconic landmark property, blending Victorian charm with modern c ...
Click For Pricing
Expedia
From $482 per night (USD)
VRBO
Luxury on Back Cove - Three Gables
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Live like a local in this grand, two‑level flat on a quiet, tree‑lined street 5 minutes from Portland’s buzzing Old Port ...
From $482 per night (USD)
VRBO
From $424 per night (USD)
Expedia
Sauna & fire table near Portland's Back Cove
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sunny open space, near Payson Park & Back Cove. Enjoy the newly added sauna in the backyard, surrounded by nature and st ...
From $424 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Whale of a Time Summa
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Whale of a Time is a perennial favorite. Located in a quiet neighborhood within walking distance to the ferry b ...
From $372 per night (USD)
VRBO
From $872 per night (USD)
Expedia
New - Cozy Cape on Peaks Island overlooking Casco Bay and Portland skyline
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
The whole group will enjoy easy access to everything from this centrally located, charming cape overlooking Casco Bay an ...
From $872 per night (USD)
Expedia
$Portland Island View 2BR Apt.\nViews of Casco Bay$
From $310 per night (USD)
VRBO
Portland Island View 2BR Apt.\nViews of Casco Bay
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy all Portland has to offer! Sunny first floor apartment in a friendly neighborhood on Casco Bay. Water views from ...
From $310 per night (USD)
VRBO
From $483 per night (USD)
Expedia
Bright, updated century old cottage two blocks from the ocean
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
*Transitioning from other STR site to VRBO so reviews and ratings are on that platform. Newly renovated 2 bedroom cotta ...
From $483 per night (USD)
Expedia
From $182 per night (USD)
VRBO
Artsy bungalow in West End Portland - Pet okay
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Sweet 1-bedroom single-family home tucked off the street in the popular West End neighborhood in Portland. This peaceful ...
From $182 per night (USD)
VRBO
From $137 per night (USD)
Expedia
NEW! Stylish Loft in the Heart of Downtown Portland
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Immaculate urban oasis in the heart of downtown Portland. Ideal for remote work. An easy walk to dozens of downtown’s mo ...
From $137 per night (USD)
Expedia
From $382 per night (USD)
VRBO
Wonderful Back Cove 2BR Apartment, Near Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Newly available beginning in August 2024, this first floor 2-bedroom apartment is perfect for your escape to Portland. T ...
From $382 per night (USD)
VRBO
From $440 per night (USD)
Expedia
Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Spacious, light-filled 3 Bedroom/1 bath 2nd-floor apartment with tasteful art, contemporary furnishings, + a well-appoin ...
From $440 per night (USD)
Expedia
From $437 per night (USD)
VRBO
A Peaceful Oasis on Munjoy Hill: 1st flr 3BR + parking
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Spacious, light-filled 3 Bedroom/1 bath 1st-floor apartment with tasteful art, contemporary furnishings, + a well-appoin ...
From $437 per night (USD)
VRBO
From $639 per night (USD)
Expedia
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
This standalone 1500sf 3-story cottage is set in an ideal location, close to the Eastern Prom, cafes, award-winning rest ...
From $639 per night (USD)
Expedia
From $463 per night (USD)
VRBO
3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Stay in the Top 2 Floors of a Charming 3-Story Cottage This spacious, light-filled retreat is in a prime location- clos ...
From $463 per night (USD)
VRBO
Click For Pricing
Expedia
Vibrant and stylish pet-friendly 2 BR apt w/king bed, downtown w/parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This 2 bedroom downtown apartment has vibrant, modern & stylish decor, yet is cozy and comfortable with a 'jungle paradi ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Munjoy Hill, Park Views, Off Street Parking
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: Everyone will enjoy easy access to everything from this centrally located place. Enjoy stunning city views fr ...
Click For Pricing
VRBO
$The Portland Getaway\n$
From $596 per night (USD)
Expedia
The Portland Getaway\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly renovated 3bd apt with historic charm and all the amenities to explore Portland's Restaurants, Arts, Coastline, Pa ...
From $596 per night (USD)
Expedia
From $382 per night (USD)
VRBO
Charming 2-Story Cottage with Hot Tub, Near Downtown and Back Cove.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Charming private guest cottage at the back of a beautiful property in the fantastic Oakdale neighborhood of Portland. Op ...
From $382 per night (USD)
VRBO
From $535 per night (USD)
Expedia
Oceanview, Handicap Friendly, Dogs & Babies Welcome. Watch the Seashore parade!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Cagasa Cottage is a friendly place originally designed for an inter-generational family with mobility issues and a dog. ...
From $535 per night (USD)
Expedia
From $540 per night (USD)
VRBO
Fall In Love With Portland!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
City of Portland Registration #4803 Live in a Comfortable Home, in Portland’s popular Munjoy Hill & Eastern Promenade a ...
From $540 per night (USD)
VRBO
From $484 per night (USD)
Expedia
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
City of Portland Registration #4803 A well cared for and comfortable home, in Portland’s popular Munjoy Hill & Eastern ...
From $484 per night (USD)
Expedia
From $118 per night (USD)
VRBO
Rosemont 1st Fl: 2BR: Sunny Spacious Convenient 21-day rental March & April '23
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
First Fl in Victorian 2-family. Your home away from home. This apartment features 1 large bedroom with queen bed and a c ...
From $118 per night (USD)
VRBO
From $688 per night (USD)
Expedia
Ocean House: Stunning Oceanfront Views, Spectacular Sunrises Peaks Island, Maine
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
**2025 DATES WILL BE OPENED MID-TO-LATE JANUARY, 2025** <b>Ocean House: A Peaks Island (Portland, Maine) Oceanfront Hav ...
From $688 per night (USD)
Expedia
From $755 per night (USD)
VRBO
Beautiful rental with private roof deck
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
One of the best locations in town! Walk to downtown and waterfront. Unit has just undergone a full renovation and includ ...
From $755 per night (USD)
VRBO
From $928 per night (USD)
Expedia
Two Beautiful apartment
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Two spacious apartments just minutes from everything! Bright colors, perfect for large families, group of friends, and P ...
From $928 per night (USD)
Expedia
From $409 per night (USD)
VRBO
Beautiful Munjoy Hill Private Oasis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This cozy, freshly remodeled apartment is fully furnished with new appliances, spectacular views of Casco Bay and the is ...
From $409 per night (USD)
VRBO
From $2819 per night (USD)
Expedia
Designer decorated in an amazing central location w/rooftop deck!
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Amazing location in Portland's West End within walking distance of everything due to central location. This building ha ...
From $2819 per night (USD)
Expedia
From $471 per night (USD)
VRBO
Ocean front cottage with private beach.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Beautiful Maine cottage with extra large porch with rocking chairs and 200 degree views of Casco Bay. Charming 2 bedroom ...
From $471 per night (USD)
VRBO
From $959 per night (USD)
Expedia
Waterfront Two Master Suite Penthouse with Rooftop
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2023 City of Portland Registration #20185280-ST Top-floor penthouse unit in historic 19th century brick building with mo ...
From $959 per night (USD)
Expedia
From $896 per night (USD)
VRBO
Old Port Penthouse Suite - Amazing Harbor Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2023 City of Portland Registration #20182242-ST Fall in love with Portland in your very own private, top-floor penthous ...
From $896 per night (USD)
VRBO
From $798 per night (USD)
Expedia
Downtown Penthouse Suite - Stunning Harbor Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2023 City of Portland Registration #20182242-ST Fall in love with Portland in your very own private, top-floor penthous ...
From $798 per night (USD)
Expedia
From $883 per night (USD)
VRBO
Penthouse Two Master Waterfront Suite with Rooftop
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2023 City of Portland Registration #20185280-ST Back-to-front top-floor penthouse suite with modern amenities, exposed b ...
From $883 per night (USD)
VRBO
From $828 per night (USD)
Expedia
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
SPRING SPECIAL!!! - book our cottage for a minimum of 3 days starting before June 12 and receive a free Ferry Vehicle ...
From $828 per night (USD)
Expedia
From $397 per night (USD)
VRBO
Luxurious 2 Bedroom Loft in Portland’s Art District
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stylishly decorated art loft walkable to the PMA and all live performance venues: Aura, Cross Arena, Merrill, Portland S ...
From $397 per night (USD)
VRBO
From $319 per night (USD)
Expedia
Peaks Island, easy to get to and harder to leave
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Peaks Island, easy to get to and harder to leave, is a wonderful place to spend time with your family. Our 2BR/1BA cott ...
From $319 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Great 2 bedroom apartment on Munjoy Hill! Private backyard - walk everywhere!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beautiful 2 bedroom, sunny, modern apartment. Deck with gorgeous view of Casco Bay. Private,peaceful, beautiful yard w ...
From $405 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Historic West End Neighborhood
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Third Floor home of a 2 residence home. 3 bedrooms include a master with CA King temperpedic bed, 2nd BR has a Queen si ...
From $459 per night (USD)
Expedia
From $500 per night (USD)
VRBO
Peaks Island Cottage with beautiful view of Whitehead passage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This well appointed seasonal cottage has everything you need to enjoy your family vacation on one of Casco Bay’s calenda ...
From $500 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Welcome to Happy Place on Peaks Island
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Immerse yourself in a historic 1890s cottage that blends vintage charm with modern comfort. This year-round retreat offe ...
From $243 per night (USD)
Expedia
From $533 per night (USD)
VRBO
Spectacular 3rd Floor Apt Near Downtown Portland
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This 1,400 sq.ft newly renovated third floor apartment is located in a quiet Oakdale neighborhood, short walk to Back Co ...
From $533 per night (USD)
VRBO
From $518 per night (USD)
Expedia
Victorian architecture dipped in refined modernity. May-June-July special!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Aged and sturdy, yet eminently modernized, this two bedroom boutique loft is perfectly situated in the heart of Portland ...
From $518 per night (USD)
Expedia
From $196 per night (USD)
VRBO
Stunning - modern 2 bedroom Victorian mansion pad
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
If it isn't the ten feet ceilings or the humongous French doors complimented by the heated radiant floors or the cozines ...
From $196 per night (USD)
VRBO
From $550 per night (USD)
Expedia
The perfect refinement of vintage seduction. May-June-July special!!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This recently remodeled open-plan living area is spacious in size and flooded with natural daylight that bounces off the ...
From $550 per night (USD)
Expedia
From $164 per night (USD)
VRBO
Ultra cool new modern flat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
“This is the best basement apartment I have seen, wow!" This historic unique one of a kind 1600sqft boutique basement a ...
From $164 per night (USD)
VRBO
From $1048 per night (USD)
Expedia
Stylish & Spacious Townhouse w/Garden, Family-friendly, walk to downtown!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Our light-filled three story home is perched on a lovely, quiet corner of the historic West End residential neighborhood ...
From $1048 per night (USD)
Expedia
From $935 per night (USD)
VRBO
Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Summer 7 day minimm (otherwise 2 night min except 3-5 nights for holidays) Gather with loved ones at Selkies' Rest: Coz ...
From $935 per night (USD)
VRBO
From $165 per night (USD)
Expedia
Back Cove Charmer Close to Everything
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sunny Fresh Newly Renovated 1 Bedroom Apt w/Queen (and separate "full" size pullout couch in living room). Well appointe ...
From $165 per night (USD)
Expedia
From $377 per night (USD)
VRBO
Classic turn of the century Maine cottage
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Come experience Maine island living in this beautifully preserved turn of the century home. Libby Cottage is located in ...
From $377 per night (USD)
VRBO
From $2253 per night (USD)
Expedia
Stunning Entire Three Units Apts (USM AREA)
Bedrooms:
6
Bathrooms:
9
Sleeps:
22
This 4200 sq.ft newly renovated entire three units apartments are located in a quiet Oakdale neighborhood, short walk to ...
From $2253 per night (USD)
Expedia
From $904 per night (USD)
VRBO
NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available.
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Panoramic Oceanfront and island view direct sunrise. Nature preserves and hiking trail next door and nearby. Away from ...
From $904 per night (USD)
VRBO
From $405 per night (USD)
Expedia
Brand new single family Munjoy Hill
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunny, art filled, new single family on Munjoy Hill. This home has been totally renovated with it’s sunny new kitchen, l ...
From $405 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Spacious Historic 1st Floor Apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
This is a charming art deco home built in 1915. The property has been recently renovated. There are many quirks of an ol ...
From $355 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Charming Great Diamond Island Cottage w/Waterviews - Bus. Lic.# STHR-003849-2021
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This quintessential Maine cottage on Great Diamond Island is as charming as it gets. You get the best of all worlds here ...
From $541 per night (USD)
Expedia
From $385 per night (USD)
VRBO
Sunny, modern, family home w large yard. Summer on beautiful Peaks Island!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Last minute cancellation - August 17 to 24. Full week or partial (4 day minimum). Full week is discounted to $250/night, ...
From $385 per night (USD)
VRBO
From $383 per night (USD)
Expedia
City Amenities, Casco Bay Sunrises and Natural Beauty
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Martin's Point high end home. This is a unique space that includes a beautiful view of Casco Bay with a waterfront park ...
From $383 per night (USD)
Expedia
From $1676 per night (USD)
VRBO
Bright, spacious home, new kitchen, hot tub, beautiful art, EV charger
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Get away to a comfortable, spacious and bright home in a quiet neighborhood with a brand new, gorgeous kitchen. A heat p ...
From $1676 per night (USD)
VRBO
From $379 per night (USD)
Expedia
Charming, Secluded, Island Getaway!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Charming, Secluded, Island Getaway for family and friends! This Down-front getaway has all the advantages to make your ...
From $379 per night (USD)
Expedia
From $654 per night (USD)
VRBO
Knit 1, Purl 2: Fabulous Turn Of The Century Cottage, Peaks Island, ME
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
There is a 7 night minimum. One of the largest and finest cottages on the less populated side of the island, it is a fu ...
From $654 per night (USD)
VRBO
From $309 per night (USD)
Expedia
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedroom Townhouse Style Unit Welcome to 255 Spring Street, Unit #10! Historic and lovingly maintained West End prope ...
From $309 per night (USD)
Expedia
From $568 per night (USD)
VRBO
Classic Turn of the Century Island Summer Cottage
Bedrooms:
1
Bathrooms:
5
Sleeps:
8
'Evergreen Anchorage' has had many roles over the last century- a 1920's guest house, a tea room and an antique store. O ...
From $568 per night (USD)
VRBO
From $1993 per night (USD)
Expedia
Art Filled East End Home a short walk to waterfront, restaurants and shops
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Exquisitely decorated, art-filled home on Portland's highly sought after East End. Stunning water views from the master ...
From $1993 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Beautifully Spacious with Charm
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beautiful spacious place located 9 minutes from downtown Portland. The property is a restored 120 year old American four ...
From $218 per night (USD)
VRBO
From $318 per night (USD)
Expedia
Classic Island Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Spacious, charming 1896 cottage at the top of quiet, magical footpath. Has a secluded, peaceful feel but is only a 2-3 ...
From $318 per night (USD)
Expedia
From $221 per night (USD)
VRBO
Charming Peaks Island Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
City of Portland license # STHR 000153 2021 2021 updates: New queen memory foam mattress , new large shower, new Rinn ...
From $221 per night (USD)
VRBO
From $818 per night (USD)
Expedia
Bright and Fresh Back Cove4 Bedroom, Sleeps 8. Airmatress for additional 2.
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
Just renovated 4 bedroom off of Back Cove Portland. Sunny, bright and open plan. Great common areas for family or reunio ...
From $818 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Hollywood meets seaside charm in the former cottage of famed director, John Ford
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
You'll feel you've got one foot in the present and the other in the past when you step over the threshold of this sweet, ...
From $426 per night (USD)
VRBO
From $818 per night (USD)
Expedia
Large, light filled 4 bedroom house - walk to ocean and ferry
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Heron's Perch on Peaks' Island has space to hold everyone and cozy spots to curl up on your own. Just steps to the marke ...
From $818 per night (USD)
Expedia
From $926 per night (USD)
VRBO
Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families
Bedrooms:
2
Bathrooms:
5
Sleeps:
14
Cindy's Place is a hidden gem located on the rocky shoreline of Peaks Island overlooking the Casco Bay and the Portland ...
From $926 per night (USD)
VRBO
From $440 per night (USD)
Expedia
Elegant condo - walk to Portland's best restaurants & Old Port
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A Foodie’s Delight Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $440 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Peaks Cottage: Modern amenities, island charm, steps to shore
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Adorable almost new Peaks Island cottage. Three bedrooms, open kitchen, living area with awesome, comfortable window sea ...
From $316 per night (USD)
VRBO
From $1594 per night (USD)
Expedia
PORTLAND PENINSULA-SPACIOUS WALKABLE EAST END SPOT
Bedrooms:
1
Bathrooms:
1
Sleeps:
12
You will not find a more ideal location for your stay In Portland! Beautifully renovated and designed with all of the am ...
From $1594 per night (USD)
Expedia
From $556 per night (USD)
VRBO
Charming Downtown Penthouse - The Cabana
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to Skyline 138! Experience the fusion of old world charm and modern comfort in this top floor apartment, nestled ...
From $556 per night (USD)
VRBO
From $937 per night (USD)
Expedia
Gorgeously renovated, 2-condo property in the West End - walk everywhere
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Four Ensuite The Heart of the West End #3 & #4 Our calendar is updated in real-time & our nightly rates are accurately ...
From $937 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Newly Renovated, Classy, and Elegant!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Bright and airy, spacious apartment just minutes from downtown! Bright colors, perfect for couples, small families, retr ...
From $348 per night (USD)
VRBO
From $1226 per night (USD)
Expedia
Contemporary Home with Historic Charm
Bedrooms:
3
Bathrooms:
6
Sleeps:
8
A recently renovated historic 5-bedroom home, formerly a Post Headquarters building. Enjoy the beautiful front porch, l ...
From $1226 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Green Goddess - Single family - Munjoy Hill
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Our newly restored, single-family home mixes Victorian architecture with vintage furnishings, local artworks, and modern ...
From $285 per night (USD)
VRBO
From $962 per night (USD)
Expedia
New Ocean-front, Peaks Island, Portland home, Beaches,
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Wonderful Ocean-front location w/ broad, breathtaking views from every room. Well appointed ,furnished, 1100 sf. year ro ...
From $962 per night (USD)
Expedia
From $197 per night (USD)
VRBO
Petit Pad Atop Munjoy Hill+Steps to Eastern Prom!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Our space is small yet cozy. Tiny living at its best. It's bright with many windows lending a glimpse of Casco ...
From $197 per night (USD)
VRBO
From $342 per night (USD)
Expedia
East End Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly renovated in 2023! The East End guesthouse is a stylish 1 bedroom apartment located parkside directly at the top ...
From $342 per night (USD)
Expedia
From $1036 per night (USD)
VRBO
Centrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Spacious Cozy 4 bedroom, 2 bath Back Cove 2nd floor condo in a lovely Portland neighborhood. Great for groups and famili ...
From $1036 per night (USD)
VRBO
From $327 per night (USD)
Expedia
Sweet Thing Summary:
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: A charming, simple retreat ideal for those looking to unplug and escape. Both of the two bedrooms overlook Diam ...
From $327 per night (USD)
Expedia

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