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Vacation rentals with a pool in New England

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in New England

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

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Home in Sag Harbor, New York, US

4.82 out of 5 average rating, 132 reviews

New! Sag Harbor Village Pool, Hot Tub &Beach House

New, immaculate, all-season home by the beach with crisp designer details. Every detail was considered for maximum enjoyment. The heated saltwater pool (open April-Nov) hot tub, fenced in yard & deck gets sun all day. Located in the village of Sag Harbor, steps from the Bay and Main Street & all the Hamptons has to offer. Come feel the vacation vibes as soon as you arrive. The central location, luxurious finishes, breathtaking sunsets on the sandy beach make this the perfect year-round getaway.

Nov 9 – 16

G$156,639 GYD per night

Guest suite in Redding, Connecticut, US

4.9 out of 5 average rating, 105 reviews

Artist Retreat in Beautiful Country Setting

Stay at this unique property, owned and designed by a Eu artist, and enjoy the quiet countryside and natural beauty that rural CT has to offer. A large one bedroom studio with an modern fireplace, is equipped with a comfortable king size bed, full bathroom, sauna, indoor resistance pool- available at an extra charge, kitchen, a dedicated workspace, and high-speed internet for seamless remote work. Relax in the evening at your own private outdoor seating area surrounded by the property's charm.

Sep 14 – 21

G$38,669 GYD per night

Home in Barnstead

4.9 out of 5 average rating, 103 reviews

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage

Immerse yourself in the New England Winter Wonderland at Locke Lake! Enjoy the beautiful scenery from the comfort of this cozy and comfortable lake house or go exploring: the Gunstock Mountain skiing area is only 25 minutes away; there are snowmobiling trails, as well as ice skating and ice fishing opportunities nearby. Time to go back in? There's more to enjoy: ping-pong, darts, board games, streaming your favorite shows in front of a fireplace and enjoying yourself away from the day-to-day.

Sep 9 – 16

G$83,273 GYD per night

Farm stay in Red Hook

4.99 out of 5 average rating, 127 reviews

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Just named one of "The 10 Best Remote AirBnBs for an Escape From Reality" according to the author of 'Leave the World Behind' Rumaan Alam First Floor open space includes a fully equipped Kitchen (Viking Range, Dishwasher, Washer/Dryer, Fridge/Freezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Gas Fireplace & Cable TV Second Floor has 2 Bedrooms: One with a King bed overlooking the paddocks One with 2 Queen beds and a Desk overlooking the pool One bathroom with shower.

Sep 21 – 28

G$135,855 GYD per night

Home in Gloversville, New York, US

4.97 out of 5 average rating, 316 reviews

Indoor Heated Pool in the Adirondacks

Year round indoor pool house that is 2000 square feet located in the lower adirondacks. There are several outdoor activities to do in the area...fishing, boating, hiking, kayaking, snowmobiling,cross country skiing & restaurants. Check out my guidebook with things to do in and around the area including near by lakes and restaurants on the lakes. Spend the day exploring and then come back to relax in the warmth of your very own private pool, sit by a fire on the patio or start the grill.

Apr 16 – 23

G$47,443 GYD per night

Home in Sag Harbor, New York, US

4.89 out of 5 average rating, 167 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence for pool area. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

Oct 24 – 31

G$96,919 GYD per night

Home in Woodstock, New York, US

4.91 out of 5 average rating, 212 reviews

Japanese Teahouse & Onsen, outside shower, tennis

Pool is open! Secluded country estate, a short drive to Woodstock, this Japanese teahouse is the ideal combination of away-from-it-all and convenience. The backyard is designed to make the most of the outdoors. Whether you’re here when the trees are turning golden brown in autumn, or when the sun shines in summer, there’s a spot outside for you. Sunny months see barbecues by the fire pit beneath, the stringed lights and swimm in the salt pool, play a game of tennis or bball and chill.

Sep 27 – Oct 4

G$52,246 GYD per night

Home in Cottekill

4.95 out of 5 average rating, 242 reviews

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

Enjoy the serenity of this contemporary home on six private acres central to all the Hudson Valley has to offer; just 20 min. from the NYS Thruway. Year-round hot tub, seasonal salt water pool, fireplace, gourmet kitchen, and large deck & patio w/ fire pit make this the ultimate getaway. Sports enthusiasts, shoppers, and diners will delight in how close we are to amazing Catskills attractions. New Paltz, Kingston, Mohonk Preserve and Minnewaska State Park are just 15 minutes away.

Oct 5 – 12

G$75,506 GYD per night

Barn in Dover-Foxcroft

4.92 out of 5 average rating, 194 reviews

Historic Maine Canoe Shop Near lake, hiking & A.T.

Over a 5-year renovation, we painstakingly converted this 120 year old Maine canoe shop into a luxe cabin experience! It has a loft with king tempurpedic bed and antique soaking tub overlooking the downstairs and out second story windows. Walk down the floating staircase to front and back doors opening up to beautiful grounds and large granite fire pit. Sink into the extra long vintage velvet sofa and watch TV, or dine under the stars outside! The YMCA indoor poos is next door.

Mar 2 – 9

G$33,837 GYD per night

Home in Stamford, Connecticut, US

4.97 out of 5 average rating, 220 reviews

Midcentury Modern ZenHouse Sculptor Studio

Zenhouse mission to inspire creativity, art, spirituality and rejuvenate.Experience complete tranquility in the Zen-like environment .Please read house rules before booking . Zen House Satori consists of an architecturally significant mid-century modern 3.5 acre private estate -main house @ Zenhouse in CT. This is the ideal setting for a memorable romantic getaway, solo adventures and business travelers – not to mention photoshoots and film locations! Inside Sculptor studio

Dec 20 – 27

G$110,073 GYD per night

Yurt in Randolph, Vermont, US

4.94 out of 5 average rating, 419 reviews

4 season Upper Yurt Stay on a VT Small Homestead

We are located in the hills of central VT, close to good hiking, skiing and swimming. Our homestead is based in permaculture landscape design. Unwind in the traditional Finnish Sauna, relax by the living pool, or kick back in an Adirondack chair looking out at the hills of VT. No cleaning fee! This is one of two listings at our place. We can accommodate groups of six by booking: 4 season Lower Yurt Stay on VT Small Farm and Tiny house on VT homestead.

Jul 23 – 30

G$15,932 GYD per night

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*

Oct 26 – Nov 2

G$227,391 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Cabins

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A space thats all yours, with room for everyone

Popular amenities for New England rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Southampton, New York, US

4.95 out of 5 average rating, 247 reviews

Southampton Village Classic

Nov 30 – Dec 7

G$183,974 GYD per night

Home in Salem, New York, US

4.98 out of 5 average rating, 180 reviews

Magical Farm Getaway - a must visit!

Nov 16 – 23

G$119,823 GYD per night

Home in Shelter Island

4.97 out of 5 average rating, 197 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Feb 28 – Mar 7

G$208,768 GYD per night

Home in Queensbury, New York, US

4.81 out of 5 average rating, 290 reviews

Rustic Lake George Mega-Lodge+Indr🔥Tub+Sauna+Pool

Nov 25 – Dec 2

G$132,098 GYD per night

Home in woodstock

4.86 out of 5 average rating, 486 reviews

CABIN WITH HOT TUB OUTDOOR FIREPLACE PIZZA OVEN

Aug 18 – 25

G$56,357 GYD per night

Home in Plymouth, Massachusetts, US

4.9 out of 5 average rating, 213 reviews

Ocean Side, Amazing View, close to town/beach, Spa

Nov 16 – 23

G$118,109 GYD per night

Home in Oak Bluffs

4.94 out of 5 average rating, 170 reviews

Spectacular beach & pool combo; beautiful sunsets!

Apr 18 – 25

G$138,827 GYD per night

Home in Magog, Canada

4.95 out of 5 average rating, 311 reviews

Lake & Mountain View Bed & Breakfast Heated Pool

May 9 – 16

G$20,281 GYD per night

Condo rentals with a pool

Condo in Saint-Faustin-Lac-Carré, Canada

4.92 out of 5 average rating, 100 reviews

**Condo SKI -IN/OUT & BEACH Mont-Blanc - Tremblant

Sep 23 – 30

G$41,559 GYD per night

Condo in Woodstock, New Hampshire, US

4.91 out of 5 average rating, 247 reviews

Luxury Studio Jacuzzi Pool White Mtns. Riverfront

Nov 29 – Dec 6

G$32,441 GYD per night

Condo in Mont-Tremblant, Canada

4.95 out of 5 average rating, 346 reviews

La Cache Dorée. The Golden Cache…

Jul 1 – 8

G$22,321 GYD per night

Condo in Lincoln, New Hampshire, US

4.95 out of 5 average rating, 566 reviews

Cozy Studio apt w/pool & hot tub Ski Loon Mountain

Aug 7 – 14

G$33,463 GYD per night

Condo in Killington

4.93 out of 5 average rating, 138 reviews

Renovated unit, prime location! Shuttle on/Ski off

Jul 19 – 26

G$31,077 GYD per night

Condo in Bartlett, New Hampshire, US

4.91 out of 5 average rating, 152 reviews

Bartlett Condo; Great Views, Resort Access

Mar 29 – Apr 5

G$37,072 GYD per night

Condo in Bartlett, New Hampshire, US

4.94 out of 5 average rating, 183 reviews

An Amazing Mountain Getaway!

Mar 18 – 25

G$39,179 GYD per night

Condo in Mont-Tremblant, Canada

4.91 out of 5 average rating, 476 reviews

Peaceful Modern Studio+Kitchen and Balcony/Parking

Oct 26 – Nov 2

G$17,435 GYD per night

Home rentals with a private pool

Home in Kerhonkson, New York, US

4.94 out of 5 average rating, 325 reviews

Country House: Rustic Charm With Modern Feel

Sep 9 – 16

G$130,537 GYD per night

Home in East Hampton, New York, US

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Nov 16 – 23

G$212,236 GYD per night

Home in Lagrangeville

4.84 out of 5 average rating, 120 reviews

Classic Hudson Valley Farmhouse Nestled in 9 Rolling Acres

Oct 22 – 29

G$128,193 GYD per night

Villa in Coxsackie, New York, US

4.99 out of 5 average rating, 80 reviews

Magnificent Hudson River Estate with Infinity Pool and Spa

Jan 19 – 26

G$239,437 GYD per night

Farm stay in Fleischmanns

4.91 out of 5 average rating, 11 reviews

Escape to a Dreamy 1857 Farmhouse in Fleischmanns

Nov 3 – 10

G$85,399 GYD per night

Bungalow in East Hampton, New York, US

4.93 out of 5 average rating, 99 reviews

East Hampton Ranch with Access to Clearwater Private Beach

May 8 – 15

G$100,060 GYD per night

Home in Lanesville, New York, US

4.77 out of 5 average rating, 205 reviews

Go Hiking and Skiing from a Family-Friendly Farmhouse

Nov 6 – 13

G$88,804 GYD per night

Home in Remsenburg, New York, US

4.95 out of 5 average rating, 64 reviews

Experience a Quiet Hamptons Getaway

Apr 4 – 11

G$125,117 GYD per night

Destinations to explore