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Holiday rentals with a pool in Pittsfield

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Pittsfield

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Cabin in Stephentown

4.84 out of 5 average rating, 238 reviews

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

2–9 Jun

$476 NZD per night

Guest favourite

Bungalow in Easthampton

4.92 out of 5 average rating, 431 reviews

The Creation Station

Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

21–28 Jul

$334 NZD per night

Guest favourite

Home in Ghent

4.87 out of 5 average rating, 270 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Escape to our recently renovated guest house on a 12-acre property, 15min from of Hudson. Cozy up in front of the wood burning stove as you take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.

23–30 Jan

$431 NZD per night

Guest favourite

Condo in Hancock

4.83 out of 5 average rating, 131 reviews

Cozy Condo @Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

19–26 Mar

$321 NZD per night

Guest favourite

Home in Woodstock

4.98 out of 5 average rating, 100 reviews

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

2–9 Sep

$1,944 NZD per night

Guest favourite

Cottage in Newfane

4.99 out of 5 average rating, 177 reviews

Cozy Vermont Antique Sugar House with Fireplace

Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

20–27 Aug

$301 NZD per night

Guest favourite

Guesthouse in Williamstown

4.93 out of 5 average rating, 219 reviews

Perfect Base for Your Berkshire Adventure

Charming private cottage with shared pool use. This newly renovated garden studio features high ceilings, a separate kitchenette with granite counters, mini fridge, microwave, queen sized bed, and rustic Arts & Crafts furniture. Located in a separate outbuilding, the cottage is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3-5.

15–22 Jun

$228 NZD per night

Guest favourite

Cottage in Rhinebeck

4.87 out of 5 average rating, 147 reviews

Secluded peaceful loft in barn by woods

La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we used a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

23–30 Apr

$294 NZD per night

Guest favourite

Guesthouse in Lenox

4.95 out of 5 average rating, 284 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

6–13 Sep

$280 NZD per night

Guest favourite

Barn in Hillsdale

4.97 out of 5 average rating, 117 reviews

Hudson Valley Hilltop Barn

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & on a 15-acre hilltop with views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking and tons of games. Perfect for winter sledding right on our hill. 100 acres of untouched nature around property. Near great shops & restaurants in Hudson & Great Barrington. *Pets must get written approval*

3–10 Sep

$1,934 NZD per night

Guest favourite

Tiny home in Ghent

4.96 out of 5 average rating, 139 reviews

Country Getaway Tiny House in woods w/Pool/Sauna

New Tiny House living space on 30 private acres with a mile of walkable trails in Beautiful Columbia County near Hudson/Chatham/Kinderhook. House has everything you need with a Queen bed, full bed, and full kitchen. The cozy space is an ideal getaway for relaxing. In the warm months enjoy the large in ground pool and renovated barn pool house. Enjoy the 6 person Sauna year round. ** Pool closed Mid-October - Mid-May, Confirm before booking.

29 May – 5 Jun

$548 NZD per night

Guest favourite

Cabin in Red Hook

4.96 out of 5 average rating, 305 reviews

Modern Upstate Cabin, near Rhinebeck NY

🏊🏽‍♂️Heated pool is open. (Will be winterized mid October Welcome to Maitopia. This beautifully designed passive glass and wood modern cabin offers elegant modern details and the warmth that only an upstate energy efficient retreat could. With a soaking egg tub, fires at every turn and a heated pool you will fall in love with the place and the towns nearby.

25 Sep – 2 Oct

$858 NZD per night

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Popular amenities for Pittsfield rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Hudson

4.93 out of 5 average rating, 227 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

13–20 Sep

$1,034 NZD per night

Guest favourite

Home in Saugerties

5.0 out of 5 average rating, 132 reviews

Upstate Modern Scandinavian Barn in the Catskills

25 Sep – 2 Oct

$1,274 NZD per night

Guest favourite

Home in Saugerties

4.96 out of 5 average rating, 150 reviews

Lux 1800's renovated farmhouse w/hot tub+pool

18–25 Oct

$2,059 NZD per night

Guest favourite

Home in Cottekill

4.95 out of 5 average rating, 242 reviews

Peace & Privacy - High Falls (hot tub & salt pool)

2–9 Dec

$671 NZD per night

Guest favourite

Home in Rhinebeck

4.96 out of 5 average rating, 164 reviews

On The Hill in Rhinebeck

22–29 Dec

$1,052 NZD per night

Guest favourite

Home in Pittsfield

4.96 out of 5 average rating, 56 reviews

Berkshire Getaway Ranch 3 acres + saltwater pool

16–23 Sep

$698 NZD per night

Guest favourite

Home in Pittsfield

4.97 out of 5 average rating, 39 reviews

Berkshire Lakefront Home W/Pool-100%Renovated

1–8 Nov

$1,396 NZD per night

Guest favourite

Home in Pittsfield

5.0 out of 5 average rating, 41 reviews

Stunning Berkshires Retreat, Large and Private

12–19 Apr

$1,450 NZD per night

Condo rentals with a pool

Guest favourite

Condo in Stratton

4.96 out of 5 average rating, 118 reviews

Cozy condo within walking distance to the slopes.

14–21 Jun

$289 NZD per night

Guest favourite

Condo in Dover

4.99 out of 5 average rating, 100 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

18–25 Sep

$346 NZD per night

Guest favourite

Condo in Dover

4.99 out of 5 average rating, 105 reviews

*Mountain Oasis: Base of Mount Snow Retreat*

12–19 Mar

$867 NZD per night

Condo in Stratton

4.88 out of 5 average rating, 107 reviews

Perfect Location! Steps to Village and Mountain

17–24 Jun

$322 NZD per night

Guest favourite

Condo in Dover

4.87 out of 5 average rating, 222 reviews

Mt Snow Ski In/Out at Seasons

4–11 Feb

$760 NZD per night

Guest favourite

Condo in Hancock

4.9 out of 5 average rating, 51 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

20–27 Sep

$274 NZD per night

Guest favourite

Condo in Hancock

4.9 out of 5 average rating, 21 reviews

All-season Berkshires ski resort condo - Sitzmark

3–10 Aug

$395 NZD per night

Guest favourite

Condo in Hancock

4.95 out of 5 average rating, 19 reviews

Upscale 2 bed/2bath Condo at a Mountain Resort!

1–8 Dec

$543 NZD per night

Quick stats about holiday rentals with a pool in Pittsfield

Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
670 reviews
Nightly prices starting at
$101 NZD before taxes and fees

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