
Vacation rentals with a pool in Fairfield County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Fairfield County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Private Hudson Valley Country Retreat
Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021

LuxeCompound-HotTub Pool Sauna Treehouse Gamebarn
Serene, elegantly appointed 19th century compound, fully modernized and set on the edge of a 50 acre land preserve next to boat friendly Bantam Lake. Located in the rolling hills of Litchfield County this expansive home has four buildings and every amenity: pool, hot tub, heated gym, cedar sauna, central AC, 2 chef’s kitchens, game barn, primary suite with wb fireplace and soaking tub, a pool house guest suite with steam shower, & treehouse w/ slides & a swing set built on a 300yr old oak tree.

Garden Level Suite with Beautiful Pool
Enjoy complete privacy and 900+ square feet of living space in the ground floor suite/apartment of our home. Complete with its own private entrance and personal garage - our ground floor suite is your own private domain. There is one king bed, one queen bed, and a comfy sectional couch. Enjoy a small kitchenette for simple cooking inside, and an alfresco BBQ for bigger cooking. There is plenty of living space inside and out! A new washer/dryer unit will take care of all the pool towels used!

The Pond Mill Retreat w/ 2 Bdrms & Pool
Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

Country Getaway - Close to Hiking & Storm King
Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

King 1BR Apt with Cozy Den and Luxury Amenities
This gorgeous apt, located in a brand-new luxury building at the center of New Haven’s historic downtown, offers unparalleled comfort, service, and amenities. You can watch a movie on a 65" HDTV, work in one of 5 co-working spaces, or relax at the pool w/ grills and cabanas. Highlights: • Walkable access to Yale • Deep-clean prior to every guest • Coffee, fresh linens, and bathroom essentials • 24/7 fitness center • Rooftop sun terrace + grills • Entertainment lounge w/ bowling alley

Cozy getaway 1 hr from NYC!
This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook! Bedroom 1: King size bed, pack n play, toddler bed. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.

Cozy, Modern Retreat in the Woods of Cold Spring
Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

A Lovely Cottage in the Woods
Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Peaceful apartment on 3.5 acres w/ Artist studio.
Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Escape to a stylish 3BR cottage with a private pool, cinema room, game room, and fire pit - perfect for families, couples, or solo travelers. Surrounded by woods and just minutes from Cold Spring, hiking trails, ski resorts, and charming shops. Relax by the electric fireplace, enjoy movie nights, play pool, or unwind with forest views from your private deck. A cozy, well-equipped retreat for peaceful getaways and Hudson Valley adventures year-round.

Luxury Hamptons Home with Heated Saltwater Pool
Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.
Popular amenities for Fairfield County rentals with a pool
House rentals with a pool

Hamptons Oasis: pool, grill, lush landscape

Entire Home (private pool), Event Friendly

Dream Home w/ Pool & Basketball Court on 3 Acres

Bluewater Lodge at Candlewood Lake

Cold Spring Mountain Retreat: Sun-filled Oasis

Arkadia House Mid-century retreat with pool & view

Log House, sits on 3acres. A retired mini farm.

Private Suite in the Heart of the Hudson Valley
Condo rentals with a pool

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

Cozy, charming retreat in Wallingford.

1856 Trading House close to water

Peaceful condo available in Westport
Other vacation rentals with a pool

Sunny 1BR Apartment

Hudson Valley Retreat | Hot Tub, Pool & Gym

Luxury Apt In Harbor Point with Balcony

The Pool Cottage at Narrow Valley Estate

GoodVibezHouse1.0~The Ultimate Couples Retreat!

Riverfront Cottage-Pool-Hot Tub-Fireplace 35m>NYC

Classic Red Barn with game room

Farm Valley Cottage + 60 ft Pool
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Rentals with beach access Fairfield County
- Rentals with lake access Fairfield County
- Fitness-friendly rentals Fairfield County
- Farmstay rentals Fairfield County
- Rentals with a kayak Fairfield County
- Townhouse rentals Fairfield County
- Rentals with a fireplace Fairfield County
- Family-friendly rentals Fairfield County
- Smoking-friendly rentals Fairfield County
- Rentals with a patio Fairfield County
- Rentals with an EV charger Fairfield County
- Apartment rentals Fairfield County
- Cabin rentals Fairfield County
- Rentals with a hot tub Fairfield County
- Rentals with a home theater Fairfield County
- Bed and breakfasts Fairfield County
- Rentals with a washer and dryer Fairfield County
- Guesthouse rentals Fairfield County
- Condo rentals Fairfield County
- House rentals Fairfield County
- Rentals with a sauna Fairfield County
- Villa rentals Fairfield County
- Rentals with breakfast Fairfield County
- Rentals with a firepit Fairfield County
- Waterfront rentals Fairfield County
- Vacation home rentals Fairfield County
- Hotel rooms Fairfield County
- Pet-friendly rentals Fairfield County
- Cottage rentals Fairfield County
- Beachfront rentals Fairfield County
- Rentals with outdoor seating Fairfield County
- Private suite rentals Fairfield County
- Rentals with pools Connecticut
- Rentals with pools United States
- Times Square
- Rockefeller Center
- Madison Square Garden
- Grand Central Terminal
- Bryant Park
- New York Public Library Main Branch
- Central Park Zoo
- MetLife Stadium
- Yale University
- Ohel Chabad-Lubavitch
- Columbia University
- The High Line
- Manhattan Bridge
- Jones Beach
- 47th–50th Streets Rockefeller Center Station
- Rough Trade
- Top of the Rock
- Yankee Stadium
- United Nations Headquarters
- Citi Field
- Empire State Building
- Fairfield Beach
- Radio City Music Hall
- Beacon Theatre




