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Vacation rentals with a pool in Windham County

Find and book unique homes with a pool on Airbnb

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Top-rated rentals with a pool in Windham County

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

Guest favorite
Home in Sturbridge
Sturbridge MA 3 BR 2 1/2 Bath Home on Cedar Lake
Fully equipped w/open lake view living space w/gas fpl. Direct access to Lake w/private dock, (2) kayaks, decks, patio, grill & fire pit. Pvt master bed/bath and 2nd bed w/lake view/deck access. Base rate up to 5 people. $50/each add pers-night max 8 total. 4th bed is futon in part finished walkout bsmt/concrete floor. Min 3 night stay pref. Base weekday $315, Weekend $365. Premium rates seasonally/holidays. Local tax added by AirBnB. Ck-out 11 AM, Ck-in 3 PM unless arranged. Sorry no more pets.
Aug 4 – 11
$305 per night
Guest favorite
Farm stay in Thompson
Rustic Farmette Studio w/ Hot Tub & seasonal pool
Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, a small family. Please include all individuals (&pets) in your booking.
Apr 12 – 19
$156 per night
Guest favorite
Home in Woodstock
Cedar Ridge
In Connecticut's "Quiet Corner", a fully renovated 2-level house bathed in sunlight, with lovely flower beds and stunning hilltop views. Relax on its patios and in its small swimming pool, stroll along its forest paths, observe birds (including birds of prey) and other wildlife. New England's "Last Green Valley National Heritage Corridor" offers multiple attractions and is home to many schools, universities, fairs, artists/artisans, farms, special events and year-round activities.
Dec 21 – 28
$243 per night

Popular amenities for Windham County rentals with a pool

House rentals with a pool

Guest favorite
Home in Montville
Casino Wine Down House***
Mar 6 – 13
$230 per night
Guest favorite
Home in Stonington
Perfect New England Getaway has a pool/ hot tub
Jan 27 – Feb 3
$450 per night
Superhost
Home in Exeter
Nature's Nook
Apr 10 – 17
$250 per night
Guest favorite
Home in Norwich
Grand 9 BR Near Casinos
Sep 2 – 9
$607 per night
Guest favorite
Home in Hopkinton
Hopkinton Mass 3+ Bedrooms - Great location!
May 15 – 22
$136 per night
Guest favorite
Home in Griswold
Secluded Lakefront 10 Acre Estate Close To Casinos
Mar 9 – 16
$743 per night
Guest favorite
Home in Norwich
Private Villa 1 mi from Casino! Plus spa amenities
May 27 – Jun 3
$124 per night
Guest favorite
Home in Montville
Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos
Jan 9 – 16
$193 per night
Guest favorite
Home in Norwich
Cozy Condo in Norwich- Minutes from Mohegan Sun
Oct 3 – 10
$132 per night
Superhost
Home in Mansfield
Mid-Century Modern Retreat
Jul 27 – Aug 3
$339 per night
Guest favorite
Home in East Haddam
5 Bedroom Country Home w. Private Pool!
Nov 12 – 19
$514 per night
Guest favorite
Home in Stonington
Homestead Near Mystic, Casinos & Beaches
Sep 26 – Oct 3
$561 per night

Condo rentals with a pool

Guest favorite
Condo in Norwich
The N-V ...The Spa at the Norwich Inn.
Apr 10 – 17
$129 per night
Guest favorite
Condo in Norwich
Renovated Condo rental at Norwich inn villa & Spa
Oct 4 – 11
$130 per night
Guest favorite
Condo in Norwich
Modern & Cozy Villa with low cleaning charge!
Jun 15 – 22
$199 per night
Guest favorite
Condo in Norwich
Peaceful Oasis steps from Mohegan Sun
Jun 29 – Jul 6
$198 per night
Superhost
Condo in Norwich
Villa Flora @ Norwich Inn & Spa
Nov 19 – 26
$175 per night
Guest favorite
Condo in Norwich
Cozy Spa Retreat-Casino-HotTub-Pools-Massage chair
Sep 30 – Oct 7
$183 per night
Guest favorite
Condo in Norwich
Luxurious Getaway-3mins to casino w/ spa amenities
Oct 23 – 30
$175 per night
Guest favorite
Condo in Norwich
Spa Creek - Chic Modern Villa near Spa & Casinos
Oct 10 – 17
$166 per night
Guest favorite
Condo in Norwich
The Vacay Villa
Apr 19 – 24
$188 per night
Guest favorite
Condo in Norwich
King Bed - hot tub - saunas - 1 mile Mohegan Sun
Jun 18 – 25
$165 per night
Superhost
Condo in Norwich
French Country Villa, near casino, newly renovated
Mar 12 – 19
$189 per night
Superhost
Condo in Norwich
Serenity Shore & Casino Villa at Norwich Inn & Spa
Aug 22 – 29
$169 per night

Destinations to explore