Vacation Rentals with Private Pool in Chatham Chamber of Commerce, MA: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Massachusetts

  5.  South Chatham
  6.  Chatham Chamber of Commerce

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80 Best Vacation Rentals with Private Pool in Chatham Chamber of Commerce (Starting from $266)

Ocean Edge Retreat
Ocean Edge Retreat
Apartment
Brewster, MA, USA
8.6k from Chatham Chamber of Commerce center

Apartments, Accommodations, Pools, Lodgings, Hot tubs, Places to stay

1 Bedroom4 Guests
6.6

Good

7 reviews

$285
Average price / night
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Enjoy your own private pool in Chatham! (2252)
Enjoy your own private pool in Chatham! (2252)
House
Chatham, MA, 02659, United States
0.4k from Chatham Chamber of Commerce center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

4 Bedrooms10 Guests
9.4

Superb

3 reviews

$867
Average price / night
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Bluegreen Dennis Port - The Soundings Seaside Resort - ST
Bluegreen Dennis Port - The Soundings Seaside Resort - ST
House
Dennis, MA, USA
8.8k from Chatham Chamber of Commerce center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

1 Bedroom2 Guests
8.0

Good

1 reviews

$266
Average price / night
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The Barn at Chatham Oaks
The Barn at Chatham Oaks
House
Chatham, MA, 02633, United States
1.0k from Chatham Chamber of Commerce center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

7 Bedrooms16 Guests
9.6

Exceptional

9 reviews

$1843
Average price / night
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Bluegreen Dennis Port - The Soundings Seaside Resort - 1BD
Bluegreen Dennis Port - The Soundings Seaside Resort - 1BD
House
Dennis, MA, USA
8.8k from Chatham Chamber of Commerce center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

1 Bedroom4 Guests
New to Booking
$396
Average price / night
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Eileen's Escape: 021-C  Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated
Eileen's Escape: 021-C Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated
House
Chatham, MA, 02633, United States
1.0k from Chatham Chamber of Commerce center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
10.0

Exceptional

9 reviews

$1190
Average price / night
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Peaceful Retreat on Chilton Lane
Peaceful Retreat on Chilton Lane
House
Brewster, MA, USA
8.8k from Chatham Chamber of Commerce center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

2 Bedrooms5 Guests
New to Booking
$508
Average price / night
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AC, Pool, Hot Tub, Fenced Yard, Beach vacation home
AC, Pool, Hot Tub, Fenced Yard, Beach vacation home
House
Chatham, MA, 02633, United States
1.5k from Chatham Chamber of Commerce center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$872
Average price / night
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Bluegreen Vacations The Soundings, an Ascend Collection Resort
Bluegreen Vacations The Soundings, an Ascend Collection Resort
Resort
Chatham Chamber of Commerce, South Chatham, Massachusetts, USA
8.8k from Chatham Chamber of Commerce center

Accommodations, Pools, Resorts, Parking, 4-star, Lodgings, Beach, Hot tubs, Places to stay

39 Bedrooms28 Guests
8.2

Very Good

94 reviews

$430
Average price / night
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Sophisticated Chatham Retreat with Private Pool and Spa RPAM093
Sophisticated Chatham Retreat with Private Pool and Spa RPAM093
House
Chatham, MA, 02633, United States
1.5k from Chatham Chamber of Commerce center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$2574
Average price / night
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Edgewater Beach Resort
Edgewater Beach Resort
Resort
Chatham Chamber of Commerce, South Chatham, Massachusetts, USA
8.8k from Chatham Chamber of Commerce center

Cheap, Accommodations, Pools, Resorts, Parking, 3-star, Lodgings, Beach, Hot tubs

76 Bedrooms12 Guests
9.1

Superb

118 reviews

$309
Average price / night
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Heated Pool AC 1/2 Mile to Beach!
Heated Pool AC 1/2 Mile to Beach!
House
Harwich, MA, 02645, United States
1.8k from Chatham Chamber of Commerce center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

8 Bedrooms20 Guests
9.8

Exceptional

16 reviews

$1323
Average price / night
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Sand, Shells & Sunsets
Sand, Shells & Sunsets
Apartment
Brewster, MA, USA
8.9k from Chatham Chamber of Commerce center

Apartments, Accommodations, Pools, Lodgings, Hot tubs, Places to stay

2 Bedrooms6 Guests
6.0

Review score

1 reviews

$475
Average price / night
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Plunge Pool, Game Barn, AC, 5 Min to Beach!
Plunge Pool, Game Barn, AC, 5 Min to Beach!
House
Chatham, MA, 02633, United States
2.0k from Chatham Chamber of Commerce center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$1142
Average price / night
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Ocean Mandevilla
Ocean Mandevilla
Apartment
Brewster, MA, USA
8.9k from Chatham Chamber of Commerce center

Apartments, Accommodations, Pools, Lodgings, Vacation rentals, Hot tubs, Places to stay

2 Bedrooms6 Guests
8.2

Very Good

7 reviews

$453
Average price / night
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Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen
Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen
House
Chatham, MA, 02633, United States
2.0k from Chatham Chamber of Commerce center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$1353
Average price / night
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Bluegreen Dennis Port - The Soundings Seaside Resort - 2BD
Bluegreen Dennis Port - The Soundings Seaside Resort - 2BD
House
Dennis, MA, USA
9.4k from Chatham Chamber of Commerce center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

2 Bedrooms6 Guests
New to Booking
$590
Average price / night
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Luxury newly renovated 4-bedroom hous.  Resort style pool in charming Chatham
Luxury newly renovated 4-bedroom hous. Resort style pool in charming Chatham
House
Chatham, MA, 02633, United States
2.0k from Chatham Chamber of Commerce center

AC, Dryer, Heater, Hot Tub, Internet, Laundry, No Smoking, Pool, Washer

4 Bedrooms10 Guests
New to Booking
$2753
Average price / night
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Breathtaking Harwich Retreat w/ Heated Pool and Spa RPAM086
Breathtaking Harwich Retreat w/ Heated Pool and Spa RPAM086
House
Harwich, MA, 02645, United States
2.0k from Chatham Chamber of Commerce center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms16 Guests
10.0

Exceptional

4 reviews

$1685
Average price / night
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Royal Retreat: 935-C  Renovated Luxury Chatham Home with Pool & Hot Tub
Royal Retreat: 935-C Renovated Luxury Chatham Home with Pool & Hot Tub
House
Chatham, MA, 02633, United States
2.1k from Chatham Chamber of Commerce center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$1591
Average price / night
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Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK
Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK
House
Chatham, MA, 02633, United States
2.8k from Chatham Chamber of Commerce center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$1187
Average price / night
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Chatham Gem with Pool & High-End Style RPAM104
Chatham Gem with Pool & High-End Style RPAM104
House
Chatham, MA, 02633, United States
3.0k from Chatham Chamber of Commerce center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
New to Booking
$3417
Average price / night
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Shore Daze: 096-C  Luxury Living in Chatham with Pool and Hot Tub
Shore Daze: 096-C Luxury Living in Chatham with Pool and Hot Tub
House
Chatham, MA, 02633, United States
3.1k from Chatham Chamber of Commerce center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

16 reviews

$1265
Average price / night
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Exclusive Harwich Haven: Pool, Spa and More RPAM068
Exclusive Harwich Haven: Pool, Spa and More RPAM068
House
Harwich, MA, 02645, United States
3.3k from Chatham Chamber of Commerce center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

4 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$2033
Average price / night
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Chatham Vacation Rental With Pool and Charm to Spare! RPAM096
Chatham Vacation Rental With Pool and Charm to Spare! RPAM096
House
Chatham, MA, 02633, United States
3.4k from Chatham Chamber of Commerce center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$1349
Average price / night
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Chatham Loop/Stage Neck/5 Bed/6 Bath
Chatham Loop/Stage Neck/5 Bed/6 Bath
House
Chatham, MA, 02633, United States
3.6k from Chatham Chamber of Commerce center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
10.0

Exceptional

43 reviews

$1922
Average price / night
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Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.\n
Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.\n
House
Chatham, MA, 02633, United States
3.6k from Chatham Chamber of Commerce center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

8 Bedrooms18 Guests
10.0

Exceptional

46 reviews

$3080
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Private Pool in Chatham Chamber of Commerce.

Where to stay in Chatham Chamber of Commerce? Best neighborhoods & areas

Chatham Chamber of Commerce Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 80 verified vacation rentals with a private pool in Chatham Chamber of Commerce. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Chatham Chamber of Commerce vary depending on the property size, location, and travel season. Rates typically start from around $266 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Chatham Chamber of Commerce also welcome pets. Currently, 18 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Chatham Chamber of Commerce often include additional features such as Pool, Private Pool, and Fireplace/Heating. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Chatham Chamber of Commerce include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.