Holiday rentals with a pool in Windham County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Windham County

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

1 of 1 pages1 / 1

Top guest favourite

The exterior of a rustic wooden house is surrounded by lush greenery and trees. A small fenced area is visible near the entrance, where a welcoming front door can be seen. The building features windows and a gabled roof, set in a tranquil natural environment.

Farm stay in Thompson

5.0 out of 5 average rating, 264 reviews

Rustic Farmette Studio w/yearround Hot Tub

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, or a family with a young kid. Please include all individuals (&pets) in your booking.

ValueLocationGrill

Top guest favourite

A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.

Home in Columbia

4.92 out of 5 average rating, 134 reviews

Breathtaking home with unforgettable views & pool!

This spacious peaceful and private home on 5 acres is great for unwinding & relaxing whether it is enjoying the day by the incredible pool/spa or stargazing at night. Far from the noise and pollution of city life. You can spend a weekend or a week away from work life because you deserve it. Close to Foxwoods casino and Mohegan sun casino, super Walmart and other stores. Please let us know before booking more than 4 people whether it is just for the day or night or both. No loud music no parties.

FamilyValueKitchen

Guest favourite

The large two-tiered deck is illuminated with soft lighting, creating a cozy atmosphere. A staircase leads to the upper level, where seating and decor are visible. An above-ground pool is situated beside the deck, surrounded by greenery and evening skies.

Home in Montville

4.92 out of 5 average rating, 333 reviews

Casino Wine Down House w/Pool, Game Room, Big Deck

Stay at the end of a quiet, cozy, cul-de-sac while minutes from local attractions. Our house is conveniently located near casinos, Mystic, vineyards, Nature's Art Village, Naval Submarine Base, CT College, USCG Academy and several beaches. Enjoy the fire pit on our large deck under the gazebo year round. In the summer cool off in the pool. In the winter relax and enjoy some cozy time under the stars in the heated igloo. Lot of fun and games! Dogs are family and always welcome at no charge.

LocationFamilyCondition

Guest favourite

The exterior of a single-story home is presented, featuring a manicured lawn and a symmetrical facade. Solar panels are installed on the roof. Large windows are visible, providing natural light to the interior. A path leads to the front door, flanked by neatly trimmed shrubs.

Home in Montville

4.91 out of 5 average rating, 261 reviews

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

Welcome to the Lucky Lounge! Minutes away from Mohegan Sun, Foxwoods, Mystic, Naval Submarine Base, USGC College, CT College, and numerous beaches. We have all you need to enjoy your time inside and outside during your stay! - Hot tub - Private pool - Fire pit - Pool table - NFL Blitz 4 player arcade game - Air hockey - Foosball - Giant connect four - Corn hole - Darts - Karaoke - Smart TV - Board games - Ultra comfy beds - BBQ - Kid friendly - Super fast WiFi - Stocked kitchen

ValueLocationBeach

Superhost

Guest house in Enfield

4.9 out of 5 average rating, 105 reviews

Close AirPort|SixFlags|Big E|Free Private Parking

Escape to Pineside Retreat in Enfield, CT—a tranquil haven blending comfort and nature. Conveniently located 20 minutes from Bradley Airport and MGM Springfield Casino, 15 minutes from Six Flags, 22 minutes from Holyoke Mall, 5 minutes from Scantic River State Park, and 10 minutes from Windsor Locks Canal State Park. Perfect for professionals or adventurers seeking relaxation in a cozy, rustic-modern retreat. Per-person pricing. Please select the correct number of guests when booking.

FamilyLocationHeating

Top guest favourite

A serene bedroom features a spacious bed adorned with white bedding and decorative pillows. Nightstands with lamps flank the bed, and a cozy couch with patterned cushions offers additional seating. Natural light filters through sheer curtains, enhancing the calming environment.

Apartment in Norwich

4.92 out of 5 average rating, 259 reviews

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf

FamilyValueTV

Top guest favourite

A historic stone farmhouse is set on a spacious green lawn, complemented by a vibrant red barn in the background. Tall trees provide shade, and a carefully arranged stone border outlines the lush garden area, creating a tranquil outdoor setting.

Farm stay in Hopkinton

4.96 out of 5 average rating, 166 reviews

1790 Stone Manor Farm

This historic New England farm and home is on almost 7 acres of land with mature gardens and places to hike, it is a warm and inviting place to spend lovely summer days by the pool and enjoy warm nights by the fire in the fall and winter. Kitchen and bathrooms all renovated. Located centrally in Ma- 90/495 interchange. Located 45 minutes from Boston, beach, history, mountains, lakes, & NE sports. This home is in historic Hopkinton, where the Boston Marathon starts, center of MA.

ValueFamilyAir conditioning

Top guest favourite

A two-story house is framed by lush greenery and vibrant flowering shrubs. The exterior showcases a combination of brick and wood, with multiple windows allowing natural light to fill the interior. A clear blue sky with scattered clouds completes the picturesque setting.

Home in Exeter

4.91 out of 5 average rating, 154 reviews

Nature's Nook

Beautifully decorated 4-bedroom, 2.5 bath house with views of nature from every window. This airy modern house on 5-acres offers: privacy, fire pits, picnic tables, a swimming pool, volleyball/badminton, basketball and giant outdoor Jenga games. Open floor plan for socializing & board games, with TV, internet & movies. Nearby hiking trails, large lake, & ski area. Wake up to the chatter of birds, breakfast on the deck and escape the constant noise & distractions of daily life.

FamilyLocationBack garden

Guest favourite

The renovated house is situated amidst lush greenery, surrounded by trees and a well-maintained lawn. A small swimming pool is visible within a fenced area, complemented by several umbrellas for shade, enhancing the outdoor ambiance on a sunny day.

Home in Woodstock

4.92 out of 5 average rating, 278 reviews

Cedar Ridge: House

HOUSE in CT’s Quiet Corner: Renovated house bathed in light, with nice stunning hilltop views. Relax on its patios and small swimming pool, stroll along its forest paths, Located in New England's "Last Green Valley National Heritage Corridor" offers multiple attractions, home to many schools, universities, fairs, artists/artisans, farms, special events and year-round activities. NOTE: RENTED DOWNSTAIRS APARTMENT. OWN PRIVATE ENTRANCE. DOES NOT SHARE OUTDOOR SPACE, PATIO, OR POOL

FamilyLocationHospitality

Guest favourite

A rustic cabin with a stone chimney is set against a backdrop of lush trees and a warm sunset. The wraparound porch features wooden railings and is complemented by neatly landscaped areas. A stone wall borders the driveway, leading to the cabin's entrance.

Cabin in Glocester

4.9 out of 5 average rating, 147 reviews

Get comfy in the country!

This special place is close to everything, making it easy to plan your visit. Just 10 minutes away from town. Secluded cabin on a 57-acre farm outlooking a large paddock with 4 highland cows. This beautiful property has a neighboring golf course and trails connecting to Heritage Park. Pool. Fireplace. Amazing sunsets! Who wouldn’t want to live like Yellowstone for a little? Home of Welcome Pastures, a Nonprofit 501(c)3 organization. Portion of proceeds go towards the foundation.

LocationValueAir conditioning

Top guest favourite

A spacious sleeping area features a canopy bed with an orange quilt. Surrounding the room are colorful artworks and wooden sculptures. Natural light enters through windows, highlighting the eclectic decor and greenery from nearby plants.

Home in Scituate

4.95 out of 5 average rating, 263 reviews

Artist studio in the woods

Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quiet, tranquil, relax. 47 minutes from Gillette Stadium.

LocationValueBiking

Top guest favourite

A modern kitchen features white cabinetry and granite countertops, equipped with a refrigerator, microwave, and stove. A small dining table is set with white chairs, and a potted plant adds a fresh touch. Natural light enters through a nearby window.

Guest suite in Brooklyn

4.94 out of 5 average rating, 241 reviews

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

FamilyLocationTV