Dorchester Area Rentals
From $333 per night (USD)VRBO
Aurora Blue - A Stylish Experience
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stylish experience at the centrally located retreat. New owners purchased East and renovated the entire home both inside ...
From $333 per night (USD)VRBO
From $1119 per night (USD)Expedia
Spacious 7-bedroom property with guest house, Wifi, AC in lovely Cambridge
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 6
Take it all in and relax at this beatiful Cambridge waterfront getaway on nearly five acres. It boasts a guest house wit ...
From $1119 per night (USD)Expedia
From $380 per night (USD)VRBO
About Time-Bunkhouse Only
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
Experience Taylors Island like a local in this 2-bedroom house. The bedrooms feature 1 queen bed and 1 twin bed, perfect ...
From $380 per night (USD)VRBO
From $412 per night (USD)VRBO
About Time-Main House
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Access to one of two full houses, see our other listing to book both houses. Perfectly set up for a multi-generational, ...
From $412 per night (USD)VRBO
From $459 per night (USD)VRBO
3-bedroom waterfront retreat in Secretary, Maryland
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your peaceful retreat in the heart of Secretary. This charming 3-bedroom home comfortably sleeps up to 6 gues ...
From $459 per night (USD)VRBO
From $263 per night (USD)Expedia
Walk to Park & River: Dog-Friendly Cambridge Gem
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Half-Mi to Historic Downtown | Covered Porch | Yard Space | Great Fishing Area Whether you’re here to explore Cambridge ...
From $263 per night (USD)Expedia
From $115 per night (USD)VRBO
Fabulous townhome in a safe community in Cambridge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Located in Cambridge, enjoy what this 2-Bedroom + Office townhome has to offer. With 1 queen bed and kids bunk beds, gue ...
From $115 per night (USD)VRBO
From $666 per night (USD)VRBO
NEW! Cattail Cove: Waterfront Retreat w/Guest House, Hot Tub, Pool,Fire Pit,Dock
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 13
Welcome to Cattail Cove, the perfect riverside escape! We want you to enjoy our gorgeous waterfront oasis where you have ...
From $666 per night (USD)VRBO
From $185 per night (USD)VRBO
Station House East: Upscale Loft in the Historic District Cambridge, MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into style and comfort in this beautifully appointed 1-bedroom, 1.5-bath condo located in the iconic Four Corners ...
From $185 per night (USD)VRBO
From $434 per night (USD)Expedia
Walk to Dtwn! Waterfront 3BR Cambridge Townhome
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Deck Overlooking the Marina | Home Office | Community Pool in Summer Embrace Eastern Shore living with a stay at this m ...
From $434 per night (USD)Expedia
From $148 per night (USD)VRBO
Pet-Friendly Pond Cottage • Nature Escape Near Beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your peaceful lakeside retreat. Escape the crowds and unwind in this charming waterfront cottage nestled amo ...
From $148 per night (USD)VRBO
From $494 per night (USD)Expedia
Waterfront Fishing Creek Cottage with Guesthouse Pier-Kayaks-Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a peaceful stay at this 2 bedroom cottage with bonus 1 bedroom guesthouse in Woolford that is near Cambridge and t ...
From $494 per night (USD)Expedia
From $367 per night (USD)VRBO
Hoopers Landing | Private Dock | Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Hoopers Landing, a delightful coastal cottage on the cheerful waterfront of Upper Hoopers Island, the first o ...
From $367 per night (USD)VRBO
From $1286 per night (USD)VRBO
4-bedroom historic waterfront farmhouse with pool in Cambridge
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This 4-bedroom historic, 19th century farmhouse is perfect for your escape to Cambridge. With a large family room with o ...
From $1286 per night (USD)VRBO
From $549 per night (USD)VRBO
Blackwater Bend | Waterfront Pool, Dock & Farm
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Blackwater Bend! Sika deer and bald eagles in the front yard, the Little Blackwater out back, and 70 acres of ...
From $549 per night (USD)VRBO
From $165 per night (USD)VRBO
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Pint-Sized on Poplar — a stylishly appointed micro-loft in the heart of downtown Cambridge, MD, sitting direc ...
From $165 per night (USD)VRBO
From $1205 per night (USD)VRBO
Multi-home Waterfront Eastern Shore Retreat with 80+ acres to yourself
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 18
Welcome to your private waterfront retreat on Maryland’s Eastern Shore. This property offers a lodge and separate barn a ...
From $1205 per night (USD)VRBO
From $767 per night (USD)VRBO
Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Riverside Haven — a beautifully designed waterfront retreat in the sought-after Deep Harbor community in Camb ...
From $767 per night (USD)VRBO
From $566 per night (USD)VRBO
Spacious 5-bedroom Chesapeake Bay Waterfront Retreat
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
Escape to a peaceful waterfront retreat in Fishing Creek, MD on the Chesapeake Bay. This spacious 5BR/4BA home sleeps 11 ...
From $566 per night (USD)VRBO
From $301 per night (USD)Expedia
Walk to Parks & Marina! Waterfront Cambridge Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stroll to Dining | Shared Grills & Picnic Area | 4 Mi to River Marsh Golf Club Sun-soaked afternoons and salty breezes ...
From $301 per night (USD)Expedia
From $251 per night (USD)VRBO
Welcome to a Cozy Waterfront Condo in Charming Cambridge, MD
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in Cambridge, MD, within a secure and gated community alongside the "Deep Harbor Marina", this cozy waterfront c ...
From $251 per night (USD)VRBO
Click For PricingExpedia
Memorial Day & Eagleman & Ironman Cozy 2BR Home near water+Fenced in back yard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay comfortably in Cambridge at this 2-bedroom house. The bedrooms feature a queen bed and a full bed, perfect for a re ...
Click For PricingExpedia
From $938 per night (USD)VRBO
Rippling Waters on Fishing Creek
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Rippling Waters on Fishing Creek, a beautifully remodeled waterfront retreat on Maryland’s Eastern Shore. Thi ...
From $938 per night (USD)VRBO
From $1452 per night (USD)Expedia
Chesapeake Bay Retreat
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Chesapeake Bay Retreat offers a tranquil escape on the Bay with stunning sunsets and ocean liner views. Guests will enjo ...
From $1452 per night (USD)Expedia
From $383 per night (USD)VRBO
Stunning Bay Views, Abundant Wildlife, Great Fishing & Easy Boating Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
A Peaceful Retreat in the Heart of Madison, MD Welcome to your perfect getaway. Nestled on a serene 1‑acre lot, this ...
From $383 per night (USD)VRBO
From $291 per night (USD)VRBO
Cozy 2BR home with AC in charming Secretary, 15 mins to downtown Cambridge MD
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Adorable 2-Bedroom Getaway Near Historic Cambridge, MD Escape to Maryland's Eastern Shore and enjoy a relaxing stay in ...
From $291 per night (USD)VRBO
From $244 per night (USD)VRBO
2BR Riverfront Retreat on 61 acres with 270 degrees of waterfront/ private Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Peaceful 2bed cottage on Church Creek with 61 private acres. Spend the day by the private riverfront pool, kayak and pad ...
From $244 per night (USD)VRBO
From $599 per night (USD)VRBO
BOAT FISH CRAB SWIM RELAX! WELCOME TO YOUR EASTERN SHORE WATERFRONT ESCAPE!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Nestled on 1½ beautifully landscaped waterfront acres with over 460' of shoreline, this private retreat offers the perfe ...
From $599 per night (USD)VRBO
From $739 per night (USD)VRBO
Waterfront Retreat on Maryland's Eastern Shore
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Wake up to breathtaking water views, enjoy your morning coffee as the sun rises over the bay, and spend your days fishin ...
From $739 per night (USD)VRBO
From $847 per night (USD)Expedia
Eastern Shore Getaway - Cambridge, Maryland
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 15
Bring the whole family to this great place with lots of room for fun. Centered in the beautiful, historic town of Cambri ...
From $847 per night (USD)Expedia
From $284 per night (USD)VRBO
Comfort by the Creek
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Single family home located on quiet cul-de-sac with access to creek via community pier. This beautiful property is the p ...
From $284 per night (USD)VRBO
From $691 per night (USD)Expedia
Modern Chesapeake Waterfront - Heated Pool - Dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Chesapeake Dream is a stunning renovated waterfront farmhouse on 5.6 acres with breathtaking Chesapeake Bay vi ...
From $691 per night (USD)Expedia
Click For PricingVRBO
Lovely Newly Renovated 3 Bed House Walk to IronMan with Off-Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to our lovely and spacious home in Cambridge with 3 bedrooms and a den that will allow you to get ready to race, ...
Click For PricingVRBO
From $1454 per night (USD)Expedia
Ironman & Eagleman - New 4-bedroom Home in Charming Cambridge
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Stay comfortably in Cambridge — your ideal base for Ironman & Eagleman! This spacious 4-bedroom home is perfectly locate ...
From $1454 per night (USD)Expedia
From $711 per night (USD)VRBO
'The Bayside Escape' Remote Chesapeake Bay Estate
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 24
Pet Friendly w/ Fee | Huge Flex Barn | Roaming Deer & Herons Disconnect to reconnect — this Fishing Creek estate is des ...
From $711 per night (USD)VRBO
From $447 per night (USD)Expedia
Walk to Cambridge Waterfront: Townhome w/ Deck
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Community Pool Access | EV Charger | On-Site Harbor Walk & Marina Experience the ultimate Eastern Shore escape at this ...
From $447 per night (USD)Expedia
From $2224 per night (USD)VRBO
Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 28
“Captains Quarters on the Bay” is the perfect place for large family reunions, corporate and religious retreats during ...
From $2224 per night (USD)VRBO