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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Massachusetts

  5.  South Chatham
  6.  Chatham Chamber of Commerce

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152 Best Vacation Rentals with Pool in Chatham Chamber of Commerce (Starting from $255)

Close2beach, Sauna, Pool, Petsok, Cantinabar
Close2beach, Sauna, Pool, Petsok, Cantinabar
House
Chatham, MA, USA
1.3k from Chatham Chamber of Commerce center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

1 Bedroom16 Guests
10.0

Exceptional

1 reviews

$2371
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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Heated Pool AC 1 2 Mile to Beach
Heated Pool AC 1 2 Mile to Beach
House
Harwich, MA, USA
1.8k from Chatham Chamber of Commerce center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

8 Bedrooms20 Guests
New to Booking
$2423
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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93 Bucks Creek Road Chatham Cape Cod - - Coastal Charm
93 Bucks Creek Road Chatham Cape Cod - - Coastal Charm
House
Chatham, MA, USA
2.1k from Chatham Chamber of Commerce center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom8 Guests
New to Booking
$2438
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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Pristine Multi-Family Home w Barn Game Room
Pristine Multi-Family Home w Barn Game Room
House
Chatham, MA, USA
2.9k from Chatham Chamber of Commerce center

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

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$1211
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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Stepping Stone Cottage
Stepping Stone Cottage
House
Chatham, MA, USA
4.0k from Chatham Chamber of Commerce center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

5 Bedrooms10 Guests
8.5

Very Good

2 reviews

$763
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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6 Harvest Hollow Drive Harwich Port Cape Cod
6 Harvest Hollow Drive Harwich Port Cape Cod
House
Harwich Port, MA, USA
4.1k from Chatham Chamber of Commerce center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
New to Booking
$1041
Average price / night
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Estate with Private pool tennis court and playground
Estate with Private pool tennis court and playground
House
Harwich, MA, USA
4.2k from Chatham Chamber of Commerce center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

9 Bedrooms18 Guests
New to Booking
$3479
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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Pool Half Mile to Beach
Pool Half Mile to Beach
House
Harwich, MA, USA
4.3k from Chatham Chamber of Commerce center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

5 Bedrooms10 Guests
New to Booking
$396
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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Wequassett Resort and Golf Club
Wequassett Resort and Golf Club
Resort
Chatham Chamber of Commerce, South Chatham, Massachusetts, USA
4.8k from Chatham Chamber of Commerce center

Luxury, Cheap, Accommodations, Pools, Resorts, Parking, Golf, Pet-friendly, 5-star

139 Bedrooms94 Guests
9.2

Superb

27 reviews

$1136
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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Sprawling Home 1 Mi to Downtown
Sprawling Home 1 Mi to Downtown
House
Harwich, MA, USA
5.6k from Chatham Chamber of Commerce center

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

7 Bedrooms14 Guests
New to Booking
$590
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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Chatham Bars Inn
Chatham Bars Inn
Resort
Chatham Chamber of Commerce, South Chatham, Massachusetts, USA
5.6k from Chatham Chamber of Commerce center

Luxury, Accommodations, Pools, Resorts, Parking, Spa, Golf, 5-star, Lodgings

156 Bedrooms51 Guests
8.8

Fabulous

48 reviews

$475
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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405 Lower County Road Unit 23 Harwich Port - Beach Bungalow
405 Lower County Road Unit 23 Harwich Port - Beach Bungalow
House
Harwich Port, MA, USA
5.7k from Chatham Chamber of Commerce center

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

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$255
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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Beautiful Harwich home with private pool in great location!
Beautiful Harwich home with private pool in great location!
House
Harwich, MA, 02645, United States
2.9k from Chatham Chamber of Commerce center

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

5 Bedrooms12 Guests
8.4

Very Good

35 reviews

$689
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
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 Pool in Chatham Chamber of Commerce.

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

Chatham Chamber of Commerce Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 152 verified vacation rentals with a pool in Chatham Chamber of Commerce. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Chatham Chamber of Commerce vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $255 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Chatham Chamber of Commerce offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Chatham Chamber of Commerce welcome pets. Currently, 27 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Chatham Chamber of Commerce often include additional outdoor features such as Pool, Fireplace/Heating, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Chatham Chamber of Commerce offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.