Vacation Rentals with Pool in Naumkeag, MA: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Massachusetts

  5.  Stockbridge
  6.  Naumkeag

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33 Best Vacation Rentals with Pool in Naumkeag (Starting from $77)

Stockbridge Retreat with Pool and Hot Tub!
Stockbridge Retreat with Pool and Hot Tub!
House
Stockbridge, MA, USA
2.0k from Naumkeag center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

4 Bedrooms10 Guests
New to Booking
$1413
Average price / night
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Stockbridge Retreat w/ Pool & Hot Tub!
Stockbridge Retreat w/ Pool & Hot Tub!
House
Stockbridge, MA, 01262, United States
2.0k from Naumkeag center

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

4 Bedrooms10 Guests
9.4

Superb

3 reviews

$1119
Average price / night
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Private Berkshire Escape Special April Pricing select your dates for discount Monthly Pricing
Private Berkshire Escape Special April Pricing select your dates for discount Monthly Pricing
House
Lee, MA, USA
2.9k from Naumkeag center

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

10 Bedrooms10 Guests
9.0

Fabulous

1 reviews

$649
Average price / night
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General Williams Estate House Lenox/Stockbridge
General Williams Estate House Lenox/Stockbridge
House
Stockbridge, MA, 01238, United States
2.4k from Naumkeag center

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

6 Bedrooms16 Guests
9.8

Exceptional

115 reviews

$1385
Average price / night
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Experience Leisure - Resort Condos in the Berkshire Hills
Experience Leisure - Resort Condos in the Berkshire Hills
Apartment
Naumkeag, Stockbridge, Massachusetts, USA
4.0k from Naumkeag center

Laundry, Pool, Hot Tub, Private Pool

8 Bedrooms24 Guests
New to Booking
$77
Average price / night
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Historic Stockbridge Villa on 25 acres sleeps 23
Historic Stockbridge Villa on 25 acres sleeps 23
House
Stockbridge, MA, 01262, United States
2.5k from Naumkeag center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

11 Bedrooms23 Guests
10.0

Exceptional

18 reviews

$932
Average price / night
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The Ponds at Foxhollow
The Ponds at Foxhollow
Resort
Lenox, MA, USA
4.9k from Naumkeag center

Cheap, Accommodations, Pools, Resorts, Parking, Lodgings, Jacuzzis, Places to stay, Family

48 Bedrooms10 Guests
8.1

Very Good

175 reviews

$209
Average price / night
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Beautiful  Farm House Near Family Ski Mountains And Other Fun Winter Activities
Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities
House
Stockbridge, MA, 01262, United States
2.6k from Naumkeag center

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

4 Bedrooms8 Guests
9.6

Exceptional

24 reviews

$770
Average price / night
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Berkshire Vacation Home in Lee - Pool is Open!
Berkshire Vacation Home in Lee - Pool is Open!
House
MA, USA
5.5k from Naumkeag center

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

5 Bedrooms12 Guests
New to Booking
$455
Average price / night
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$5,500/mo Special * Private Berkshire Escape*
$5,500/mo Special * Private Berkshire Escape*
House
Lee, MA, 01238, United States
2.9k from Naumkeag center

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

4 Bedrooms10 Guests
9.6

Exceptional

18 reviews

$848
Average price / night
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Wellspring by AvantStay Indoor Pool Views
Wellspring by AvantStay Indoor Pool Views
House
Richmond, MA, USA
7.2k from Naumkeag center

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

1 Bedroom12 Guests
New to Booking
$960
Average price / night
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Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee
Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee
Apartment
Lee, MA, 01260, United States
3.6k from Naumkeag center

AC, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Pool

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$260
Average price / night
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Charming 2-bedroom apartment in Lee with fitness room, WiFi
Charming 2-bedroom apartment in Lee with fitness room, WiFi
Apartment
Lee, MA, 01260, United States
3.8k from Naumkeag center

AC, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Pool

2 Bedrooms6 Guests
8.8

Fabulous

3 reviews

$263
Average price / night
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Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee
Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee
Apartment
Lee, MA, 01260, United States
3.8k from Naumkeag center

AC, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Pool

2 Bedrooms6 Guests
New to Booking
$263
Average price / night
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Spacious 4BR Central-Berkshires Home with POOL!
Spacious 4BR Central-Berkshires Home with POOL!
House
Lee, MA, 01238, United States
3.9k from Naumkeag center

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

4 Bedrooms9 Guests
10.0

Exceptional

3 reviews

$372
Average price / night
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🏠Great Clean+Comfy 2/2 Lee! LR/DR/K(Open)! Pool,FP,Jacuzzi,Gym+KidsStuff! A/C🌞
🏠Great Clean+Comfy 2/2 Lee! LR/DR/K(Open)! Pool,FP,Jacuzzi,Gym+KidsStuff! A/C🌞
Condo
South Lee, MA, 01260, United States
4.0k from Naumkeag center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

2 Bedrooms6 Guests
New to Booking
$328
Average price / night
Check Availability
Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee
Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee
Apartment
Lee, MA, 01260, United States
4.1k from Naumkeag center

AC, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Pool

2 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$262
Average price / night
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Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee
Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee
Apartment
Lee, MA, 01260, United States
4.3k from Naumkeag center

AC, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Pool

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$258
Average price / night
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Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
Condo
Lee, MA, 01238, United States
4.7k from Naumkeag center

AC, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$510
Average price / night
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Modern Log Cabin with Saltwater Pool & Mountain Views By Evergreen Home
Modern Log Cabin with Saltwater Pool & Mountain Views By Evergreen Home
House
West Stockbridge, MA, 01266, United States
4.8k from Naumkeag center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms9 Guests
New to Booking
$852
Average price / night
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Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
House
Lenox, MA, 01240, United States
4.8k from Naumkeag center

AC, Arcade, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater

5 Bedrooms14 Guests
9.4

Superb

63 reviews

$547
Average price / night
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Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate
House
Lee, MA, 01238, United States
4.9k from Naumkeag center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
7.8

Good

6 reviews

$565
Average price / night
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Lots of snow! Ski, snowshoe/ heated pool\n- fabulous in beautiful Stockbridge
Lots of snow! Ski, snowshoe/ heated pool\n- fabulous in beautiful Stockbridge
Condo
West Stockbridge, MA, 01266, United States
5.3k from Naumkeag center

AC, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$285
Average price / night
Check Availability
Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!
Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!
Condo
Lee, MA, 01238, United States
5.4k from Naumkeag center

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

4 Bedrooms14 Guests
10.0

Exceptional

4 reviews

$374
Average price / night
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3-bedroom furnished townhome near Lenox, beautiful views, 3 month min rental
3-bedroom furnished townhome near Lenox, beautiful views, 3 month min rental
House
Lenox, MA, 01240, United States
6.6k from Naumkeag center

AC, Dryer, Free Parking, Heater, Laundry, Microwave, No Smoking, Pool, TV

3 Bedrooms6 Guests
New to Booking
$330
Average price / night
Check Availability
Fabulous Apartment - Great Barrington
Fabulous Apartment - Great Barrington
Apartment
Great Barrington, MA, 01230, United States
6.9k from Naumkeag center

AC, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$248
Average price / night
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Expansive Mountainside Escape by Evergreen Home
Expansive Mountainside Escape by Evergreen Home
House
West Stockbridge, MA, 01266, United States
7.0k from Naumkeag center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$1363
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 Naumkeag.

Naumkeag Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 33 verified vacation rentals with a pool in Naumkeag. 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 Naumkeag vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $77 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Naumkeag 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 Naumkeag welcome pets. Currently, 6 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 Naumkeag often include additional outdoor features such as Pool, Fireplace/Heating, and Bedding/Linens. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Naumkeag 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.