Pinkwink Pond Rentals
- From $550 per night (USD)
VRBO
4 Bedrooms, 2 Baths, Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Location! Location! Location! This is classic cape cod home with four bedrooms, 2 bathrooms and an outdoor shower. The ...
From $550 per night (USD)VRBO
- From $395 per night (USD)
Expedia
Pet friendly and waterfront!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful home overlooking Emery Pond has been completely renovated. Spacious 3 bedroom 1 and half bath home with ...
From $395 per night (USD)Expedia
- Click For Pricing
VRBO
Pet Friendly in Riverbay! Nicely furnished 3 bedroom, 2 full bath home in quiet Riverbay.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Perfect home for a family vacation! Nicely furnished 3 bedroom, 2 full bath home in quiet Riverbay. There is a queen be ...
Click For PricingVRBO
- From $434 per night (USD)
Expedia
Updated Chatham Inn Home | Spacious Deck & Private Heated Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Stepping Stones -- Old Chatham Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $434 per night (USD)Expedia
- From $264 per night (USD)
VRBO
Deeded Rights to Emery Pond Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 16646 - Sunny-Side-Up: Deeded Rights to Emery Pond Fire Pit! The Space: Spend a week where the sun always shin ...
From $264 per night (USD)VRBO
- From $457 per night (USD)
Expedia
Spacious home in quiet neighborhood!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious three bedroom, two and half bath home in Riverbay offers plenty of living space on a 1/2 acre wooded corner lot ...
From $457 per night (USD)Expedia
- From $429 per night (USD)
VRBO
Dog friendly! Enjoy outdoor space with large yard, patio, and enclosed outdoor shower!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Plan your family vacation in this 4 bedroom, 3 bath home that sleeps 10. Plenty of room to spread out with a living roo ...
From $429 per night (USD)VRBO
- From $267 per night (USD)
Expedia
Waterfront on Private Lake!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: 16644 - Lover's Lookout: Waterfront on Private Lake! The Space: Enjoy your best days of summer at our waterfro ...
From $267 per night (USD)Expedia
- From $200 per night (USD)
VRBO
WALK TO RESTAURANTS, SHOPS & LIQUOR STORE - CLOSE TO DOWNTOWN CHATHAM!!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This adorable cottage is in an ideal location in West Chatham! Located on a quiet cul-de-sac with five other homes. A 5 ...
From $200 per night (USD)VRBO
- From $268 per night (USD)
Expedia
Quintessential Chatham Cottage by the Pond
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
If a true Cape Cod cottage is what you are looking for, your search ends here. Steps from Schoolhouse Pond, you can for ...
From $268 per night (USD)Expedia
- From $439 per night (USD)
VRBO
Great Chatham Location w\/ Hot Tub, Near Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 16650 - The Beach Buoys: Great Chatham Location w/ Hot Tub, Near Beach! The Space: Access to beaches, a quinte ...
From $439 per night (USD)VRBO
- From $449 per night (USD)
Expedia
Walk to Ryder Cove Wet Bar & Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: 16651 - Smooth Sailing: Walk to Ryder Cove Wet Bar & Hot Tub! The Space: Keep it classy this summer and spend ...
From $449 per night (USD)Expedia
- From $221 per night (USD)
VRBO
Spacious w\/ Large Outdoor Area Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16637 - The Driftwood: Spacious w/ Large Outdoor Area Fire Pit! The Space: Our beautifully decorated, spacious ...
From $221 per night (USD)VRBO
- From $263 per night (USD)
Expedia
Updated Chatham cottage with privacy, nautical decor and lovely backyard.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Updated Chatham cottage set back from the road for privacy and nautical decor throughout. There is a gourmet kitchen wit ...
From $263 per night (USD)Expedia
- From $230 per night (USD)
VRBO
Beautifully Renovated Cape on Bike Trail, 1 mile to Downtown Chatham and Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Charming Cape house recently renovated less than a mile to Downtown Chatham for shopping and restaurants. Located on a q ...
From $230 per night (USD)VRBO
- From $532 per night (USD)
VRBO
Perfectly located, with central AC. 3BR, sleeps 6-8
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Our house has undergone a complete renovation with all new updates. The house has a complete master suite on the first ...
From $532 per night (USD)VRBO
- From $408 per night (USD)
VRBO
North Chatham - Charming \"Stones Throw\"
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located outside of downtown Chatham sits this charming four bedroom home, known as Stones Throw. This property features ...
From $408 per night (USD)VRBO
- Click For Pricing
Expedia
Modern Luxury in Chatham with Water Views: 875-C
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
This property is professionally managed by Pretty Picky Properties June rates just reduced! Modern Luxury in Chatham wi ...
Click For PricingExpedia
- From $416 per night (USD)
VRBO
Near Beach, bike trail, Central AC, WiFi, Private Neighborhood
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
5 Bedroom- 3 Bathroom- Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $416 per night (USD)VRBO
- From $750 per night (USD)
Expedia
Pet friendly cottage on White's Pond! Serene water views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Dog friendly on White's Pond! Sip your morning coffee on the deck of this lovely two story cottage directly on White Po ...
From $750 per night (USD)Expedia
- From $595 per night (USD)
VRBO
New July dates! Sun drenched Cape haven- spectacular deck, garden & patio!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Relax and revive in this airy, modern and beautifully appointed 2600 square ft. Cape Cod home in a lovely secluded neigh ...
From $595 per night (USD)VRBO
- From $1355 per night (USD)
VRBO
Apres Sea - Chatham 4 Bedroom w\/ Central AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Ideal location just minutes to bike trail, beaches and downtown Chatham! This home is represented by Nauset Rental, a l ...
From $1355 per night (USD)VRBO
- From $284 per night (USD)
VRBO
Pool Table, Bar, Ping Pong, Sun Rm, Deck,4 BR, Private
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This North Chatham 4 BR home with central AC has plenty of room for families to spread out and enjoy a relaxing Chatham ...
From $284 per night (USD)VRBO
- From $375 per night (USD)
VRBO
BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Vivian's Hideaway! Experience all that Cape Cod has to offer in an amazing indoor and outdoor living space, n ...
From $375 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Perfect couples escape. Close to beaches, great biking & walking & pet friendly.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This open studio apartment is the perfect stay. Privacy, beach proximity, pet friendly and CLEAN. Lots to do and see in ...
From $400 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Reuben Young House: circa 1820 newly renovated
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming antique newly renovated. close to downtown Chatham (1.5 miles). Close to Fish Pier, Ryders Cove, Oyster Pond, c ...
From $850 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Excellent Chatham Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This Chatham beauty is a Newly built cottage which is walking distance to Pleasant Bay and a short drive to town. A per ...
From $450 per night (USD)VRBO
- From $780 per night (USD)
VRBO
CHATHAM WATER FRONT\/VIEW HOUSE FIRST TIME RENTAL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perfect vacation spot. Enjoy your vacation on this 3 bedroom 2 bath, Central air conditioned house bordering Emery Lake ...
From $780 per night (USD)VRBO
- From $1173 per night (USD)
VRBO
Chatham Landmark Estate, Large Guest House, Pool 177-CF
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 18
This property is professionally managed by Pretty Picky Properties Chatham Landmark Estate, Awesome Barn/Guest House, P ...
From $1173 per night (USD)VRBO
- From $1043 per night (USD)
VRBO
Perfect House to Enjoy Family & Friends!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Main house has 3 bedrooms 2 baths. Open floor plan is great for a big group. Apartment has a full kitchen, living area a ...
From $1043 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Sun-filled Completely Renovated 3 BR-2B minutes from Pleasant Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sun Filled, Completely Renovated 3 Bedroom, 2 Bath Minutes from Pleasant Bay or Downtown, Perfect for your Cape Adventur ...
From $350 per night (USD)VRBO
- From $714 per night (USD)
VRBO
Perfect spot to kayak or canoe
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 13
Enjoy this Special Waterfront Retreat on Ryders Cove, a Perfect Spot to Kayak or Canoe! This 5 bedroom, 3.5 bath home ...
From $714 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Centrally located home with patio, a\/c included, walking distance from town.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Centrally located vacation home with central air conditioning in an ideal location with 3 bedrooms, 2 full baths plus ...
From $500 per night (USD)VRBO
- From $280 per night (USD)
Expedia
On Goose Pond Pet Friendly Wifi Water Views Private
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 Bedroom- 1 Bath- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $280 per night (USD)Expedia
- From $684 per night (USD)
VRBO
Lover's Lake Escape - Chatham Lakefront home with private access to Lover's Lake
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This home is represented by Nauset Rental, a local vacation rental management company. Enjoy the serenity of Lover's L ...
From $684 per night (USD)VRBO
- From $625 per night (USD)
VRBO
Sand Dunes and Salty Air - 5 minutes drive to beaches!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A beautiful house on a quiet cul-de-sac that is close to everything that Chatham has to offer. It is less than 2 miles f ...
From $625 per night (USD)VRBO
- From $712 per night (USD)
VRBO
Superb, Upscale with Pool and Hot Tub in Chatham: 002-C
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This Property is professionally managed by Pretty Picky Properties. Superb, Upscale with Pool and Hot Tub in Chatham S ...
From $712 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Pondfront cottage on Stillwater Pond
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Set your clocks back 50 years, and fish for your breakfast from your own dock or row-boat. This setting has been descri ...
From $360 per night (USD)VRBO
- From $595 per night (USD)
VRBO
Lake front, Near Beach, AC, WiFi, Pet Friendly near Bike Path
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedroom - 2.5 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $595 per night (USD)VRBO
- From $285 per night (USD)
VRBO
Walk to School House Pond in Chatham.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This 2500sq ft house is 8yrs old and offers all the toys including a hot tub, sauna, bikes and kayaks for guest use. Fro ...
From $285 per night (USD)VRBO
- From $875 per night (USD)
VRBO
Charming Waterfront House in Chatham
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
Very private lakefront setting with spectacular views and private beach. Filled with Charm. It was the original Ice Hous ...
From $875 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Chatham rental ~ 4 bed\/3ba ~ walk to the beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
WALK TO JACKKNIFE COVE BEACH in Chatham from this charming, clean, and well-kept home. Enjoy s'mores with the kids at ou ...
From $600 per night (USD)VRBO
- Click For Pricing
VRBO
Waterfront Property with Private Access to Ryder's Cove and Short Walk Down Path to Sandy Association Beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy this beautiful waterfront location on Ryders Cove. Large yard and beautiful outdoor space with water views make th ...
Click For PricingVRBO
- Click For Pricing
VRBO
Sail Away - A North Chatham Getaway walking distance to Crow's Pond
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Tucked away in beautiful North Chatham, this 5 bedroom 3 bath Cape is absolutely perfect for an extended family get-away ...
Click For PricingVRBO
- From $423 per night (USD)
VRBO
Beautiful home near Jacknife Beach and bike trail
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This newly renovated home has 3 bedrooms and 2 1/2 baths,and is located in a nice quiet neighborhood. This home is centr ...
From $423 per night (USD)VRBO
- From $525 per night (USD)
VRBO
Stylish Cape in North Chatham ~ Walk to Private Neighborhood Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful cape in upscale Harbor Cove neighborhood. Recently renovated with all new furnishings and appliances. 4 BRs, 2 ...
From $525 per night (USD)VRBO
- From $278 per night (USD)
VRBO
Pet friendly home with central air
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This adorable PET FRIENDLY cape style home is located on a peaceful, residential, dead end road, close to two fresh wate ...
From $278 per night (USD)VRBO
- From $233 per night (USD)
Expedia
Large Home w\/ Fire Pit and Dogs Welcome!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16674 - Heatherwood Haven: Large Home w/ Fire Pit and Dogs Welcome! The Space: Escape to Chatham, where baysid ...
From $233 per night (USD)Expedia
- Click For Pricing
VRBO
Water view - Chatham house and boathouse
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 17
A beautiful Chatham home on Ryder's Cove. Plenty of space for an extended family. This listing has both a main house and ...
Click For PricingVRBO
- From $208 per night (USD)
Expedia
Gorgeous Home with Game Room Dog Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 16675 - Summer Stunner: Gorgeous Home with Game Room Dog Welcome! The Space: Another Cape Cod vacation means a ...
From $208 per night (USD)Expedia
- From $399 per night (USD)
VRBO
Sunny Waterfront Home Perfect for Cape Cod Getaway!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Soak up the sun while enjoying the lush outdoor space at our waterfront home, Queen’s Quarters. Bring or rent a kayak or ...
From $399 per night (USD)VRBO
- From $363 per night (USD)
Expedia
Spacious Deck, Large Yard & Dogs Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16676 - Shore Break: Spacious Deck, Large Yard & Dogs Welcome! The Space: Chatham is known for its delicious f ...
From $363 per night (USD)Expedia
- From $282 per night (USD)
VRBO
Bright home walking distance to Main Street with great patio, firepit & bikes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Queen Anne Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $282 per night (USD)VRBO
- From $183 per night (USD)
Expedia
Inviting apartment with patio, kitchenette, & golf nearby
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Reynard's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $183 per night (USD)Expedia
- From $1016 per night (USD)
VRBO
THE CHATHAM TREEHOUSE 7 minutes from the Village
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Treehouse, just 7 mins from the village of Chatham! This beautiful, private property is nestled in the wo ...
From $1016 per night (USD)VRBO
- From $388 per night (USD)
Expedia
Chatham Getaway w\/ Trail Access, 2 Mi to Beaches!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your next exciting Cape Cod adventure awaits at this cozy Chatham vacation rental! Perfect for a memorable family getawa ...
From $388 per night (USD)Expedia
- From $809 per night (USD)
VRBO
Chatham~Lake Front~Shark Free Swimming!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This phenomenal home has been completely renovated over the past few years down to the addition of central air, wood flo ...
From $809 per night (USD)VRBO
- From $1459 per night (USD)
Expedia
Superb, Upscale Waterfront in North Chatham: 078-C
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This Property is professionally managed by Pretty Picky Properties. Superb, Upscale Waterfront in North Chatham Sleeps ...
From $1459 per night (USD)Expedia
- From $988 per night (USD)
VRBO
Luxurious Home with Pool & Game Room in Cape Cod
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to our newly listed vacation home in Chatham, Cape Cod! This spacious 4-bedroom/4.5-bathroom house is a haven fo ...
From $988 per night (USD)VRBO
- From $554 per night (USD)
Expedia
Pet friendly home with large backyard!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Enjoy your Chatham vacation at this spacious, 5 bedroom, 2 bath home. Offering 2 queens, a bunk bed and 4 twins, and a t ...
From $554 per night (USD)Expedia
- From $786 per night (USD)
VRBO
Lovely 3 BR Home in Harbor Coves, North Chatham...Peaceful Setting!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This lovely cape with 3 bedrooms and 2 1/2 baths sits privately on over an acre of land. A classic, antique home filled ...
From $786 per night (USD)VRBO
- Click For Pricing
VRBO
Spacious and beautiful home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful and welcoming property for a group of family or friends looking to have a wonderful time. Quiet and peaceful ...
Click For PricingVRBO
- From $512 per night (USD)
VRBO
Updated 6 Bedroom Home Close to Everything!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Cranberry Corners is the perfect house for your extended family vacation! DOGS WELCOME! Plenty of space to spread out, ...
From $512 per night (USD)VRBO
- From $857 per night (USD)
Expedia
Located in quiet Riverbay directly on the river; kayak to Jacknife Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
OFF SEASON RATES REDUCED!! Kayak to Pleasant Bay on Muddy River straight from the backyard (kayaks are provided). This ...
From $857 per night (USD)Expedia
- From $582 per night (USD)
VRBO
Views of Eastward Ho Golf Course from the backyard!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
North Chatham gem offers views of Eastward Ho Golf Course from the backyard! Antique Cape style home that sleeps 8 peopl ...
From $582 per night (USD)VRBO
- From $745 per night (USD)
Expedia
KAYAK TO PLEASANT BAY FROM YOUR BACK YARD! KAYAKS PROVIDED!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
***KAYAK TO PLEASANT BAY FROM YOUR BACK YARD! KAYAKS PROVIDED! OPEN YEAR ROUND Spacious five bedroom, four bath ho ...
From $745 per night (USD)Expedia
- From $230 per night (USD)
VRBO
Dog-friendly home with yard, patio, grill, & fireplace - great location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Whale's Tales Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $230 per night (USD)VRBO
- From $321 per night (USD)
Expedia
Waterfront on Pond w\/ Private Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: 16664 - Family Tides: Waterfront on Pond w/ Private Beach! The Space: This beautiful waterfront property, loca ...
From $321 per night (USD)Expedia
- Click For Pricing
VRBO
Spacious Cape - Large Private Backyard, 3 Decks!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
All bathrooms and kitchens recently renovated. Fast 1GB internet, full cable, multiple living areas, work from home frie ...
Click For PricingVRBO
- From $550 per night (USD)
VRBO
Perfect Chatham Retreat | Access To Lovers Lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
*Cancellation policy at end of property description.* Enjoy your best days of summer at this 2BR + Bonus custom home ...
From $550 per night (USD)VRBO
- From $1109 per night (USD)
VRBO
Gorgeous Cape Cod getaway with patio, grill, sun room, fireplace, AC, & W\/D
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Deer Meadow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $1109 per night (USD)VRBO
- Click For Pricing
Expedia
Secluded hilltop home at Chatham, with a fenced yard, Pet\/family\/work-friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
*** New Installed Ductless Mini Split heating/AC System *** Nestled atop a secluded hill overlooking the picturesque Mon ...
Click For PricingExpedia
- From $349 per night (USD)
VRBO
Cape Escape - Two Bedroom, Two Bathroom Near Beaches and Cycling
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedroom- 2 Bath- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $349 per night (USD)VRBO
- From $1714 per night (USD)
Expedia
PRIVATE HEATED POOL!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Private pool! Vacation near the beach in this charming 4 bedroom (King/king/queen/queen) and 2.5 bath home with private ...
From $1714 per night (USD)Expedia
- From $718 per night (USD)
VRBO
Chatham Compound + Carriage House - Huge yard, Game Room, Kayaks, Sleeps 10
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Newly Listed to VRBO. Also listed on Airbnb, with 37 reviews and a 4.97 star rating! This beautiful family home is ever ...
From $718 per night (USD)VRBO
- From $523 per night (USD)
Expedia
On Top of Chatham, Updated, Three Level Living: 048-CH
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This property is professionally managed by Pretty Picky Properties On Top of Chatham, Updated, Three Level Living New ...
From $523 per night (USD)Expedia
- From $283 per night (USD)
VRBO
Exclusive Neighborhood 1\/2 mi from Jackknife Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16671 - Whitecap: Exclusive Neighborhood 1/2 mi from Jackknife Beach The Space: Experience the quintessential ...
From $283 per night (USD)VRBO
- From $437 per night (USD)
Expedia
Modern and Chic 3BR Home in Chatham, Close to Town: 041-CE
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This property is professionally managed by Pretty Picky Properties Modern and Chic 3BR Home in Chatham, Close to Town ...
From $437 per night (USD)Expedia
- From $2336 per night (USD)
VRBO
Superb Luxury Home in Chatham with New Heated Salt Water Pool: 023-CJ
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This property is professionally managed by Pretty Picky Properties Superb Luxury Home in Chatham with New Heated Salt W ...
From $2336 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Newly renovated house 3 minutes to Wequassett Resort and 7 minutes to CBI.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Relax with the whole family at this peaceful place to stay. A stunning, fresh, contemporary home in Chatham! Perched upo ...
From $850 per night (USD)VRBO
- From $635 per night (USD)
VRBO
Waterfront Chatham home, walk to downtown, minutes to several beaches!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy Chatham cottage with private lake access and minutes to downtown and beaches! This house is perfect for families o ...
From $635 per night (USD)VRBO
- Click For Pricing
Expedia
The Rose Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the enchanting Rose Cottage, a hidden gem nestled in the heart of Chatham, Massachusetts. This picturesque re ...
Click For PricingExpedia
- From $589 per night (USD)
VRBO
Wonderful dog-friendly rental close to downtown Chatham and Oyster Pond Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
New for 2024!! Wonderful dog friendly rental for the whole family, with access path to a private beach deeded at White's ...
From $589 per night (USD)VRBO
- From $1648 per night (USD)
VRBO
Large, beautiful home with extraordinary design features and bonus rooms galore
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 12
This large, gorgeous home is perfect for entertaining, set on an acre of land with a private yard and large patio. The h ...
From $1648 per night (USD)VRBO
- From $787 per night (USD)
VRBO
Chatham Vacation Rental With Pool and Charm to Spare!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located in one of Cape Cod’s premier resort towns, 764 Riverview Drive offers everything a discerning vacationer is look ...
From $787 per night (USD)VRBO
- From $1538 per night (USD)
VRBO
Renovated Luxury Chatham Home with Pool & Hot Tub: 935-C
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This property is professionally managed by Pretty Picky Properties Renovated Luxury Chatham Home with Pool & Hot Tub Ho ...
From $1538 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Beautiful Chatham
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This property is located in the Ryder's Cove area of Chatham MA. The main house consist of 2 bedrooms on the upper leve ...
From $600 per night (USD)VRBO
- From $446 per night (USD)
VRBO
Robin's Nest - Dog Friendly Chatham 4 Bedroom
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This home is represented by Nauset Rental, a local vacation rental management company. Beautiful, spacious 4 bedroom, 2 ...
From $446 per night (USD)VRBO
- Click For Pricing
VRBO
Gorgeous Year round private beach property ready to move in! Flexible terms!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Private beach, 5 bedroom 3 bath 3 full floors living on private location between two 5 star resorts! Excellent restauran ...
Click For PricingVRBO
- From $643 per night (USD)
VRBO
5 Bedroom Chatham Charmer
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Located in the highly desirable town of Chatham, this five bedroom, three bath rental home will meet all your vacation n ...
From $643 per night (USD)VRBO
- From $786 per night (USD)
VRBO
Large Chatham Rental w\/ 5 Bedrooms w\/ 5 Private Bathrooms
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
This stunning rental home is a vacationer’s dream! Easy and close access to the ponds, bike trails, conservation area a ...
From $786 per night (USD)VRBO
- From $569 per night (USD)
VRBO
Perfectly Located 3 Bedroom Chatham Charmer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Location is everything! The perfectly appointed 3 bed, 2 full bath home is just 1.3 miles to Chatham Main Street, 1.3 Mi ...
From $569 per night (USD)VRBO
- From $443 per night (USD)
VRBO
Chatham pond access with view
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy our large back yard and private road that leads to the Pond behind the house, for fishing, non-motor boating, padd ...
From $443 per night (USD)VRBO
- From $755 per night (USD)
VRBO
Gorgeous, Modern, Dog Friendly Chatham 4 Bedroom with Central AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This home is represented by Nauset Rental, a local vacation rental management company. Gorgeous, modern beach house out ...
From $755 per night (USD)VRBO
- From $1166 per night (USD)
VRBO
Waterfront Renovated Home with Pool and Dock: 560-C
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Waterfront Renovated Home with Pool and Dock Sleeps 8 Rents Friday - Friday during peak season Pets Considered It's r ...
From $1166 per night (USD)VRBO