
Holiday rentals with a pool in New Milford
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in New Milford

Total holiday rentals
Explore 20 holiday rentals in New Milford

Nightly prices starting at
New Milford holiday rentals start at $126 AUD per night before taxes and fees

Verified guest reviews
Over 680 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of New Milford holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across New Milford rentals

4.9 Average rating
New Milford stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in New Milford
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

4Br Mountain Brook House on 130 acres w/ trails
Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
Looking for privacy, seclusion, and direct access to Sleeping Giant State Park right from your back yard? Then look no further! Entire Mid Century home centrally located to many great attractions and colleges. Featuring an open floor plan characterized by large glass windows and open space featuring simplicity and an integration with nature. Access to I-91 or Rt15 are both about 1 mile away, with Yale University and Downtown New Haven about a 20 minute drive. Farmington Canal bike trail-.5 miles

Modern Upstate Cabin, near Rhinebeck NY
[ 🏊🏽♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Magic Red Barn with Heated Salt Pool (opened now)
Escape to magic, just one hour from NYC. No car really necessary. Immerse yourself in nature’s wonderland: wildflowers, scenic trails, and vibrant local farmers’ markets. Unwind in a heated saltwater pool (summer) and cedar soaking tub (winter). Sleep in a stunning renovated loft — 1,000 sq ft of luxury in a private barn. Ideal for family or friends: 1 king, 2 queens, and a toddler bed. Full kitchen with oven, microwave, and half fridge. Fiber optic Wi-Fi. Privacy guaranteed: no other guests.

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️
PLEASE READ ALL HOUSE RULES PRIOR TO INQUIRIES AND BOOKINGS! 1 night/longer stays can be accommodated upon request and calendar availability. “Home Is Where The Heart Is”. If you love tranquility and coziness combined with sophistication and traditional rural charm, this is the place for your stay (only 4 miles from Beacon). The ground floor apartment with a private entrance (located around the back in a private house) includes a living room, full kitchen, full bathroom and Queen bedroom

Private lofted retreat with Steam room HotTub/Pool
Take it easy at this unique and tranquil getaway. off NYS thruway close to local restaurants/shops 5 min from town of Saugerties & Hits 25 min from Hunter Mt Skiing 15 min from town of Woodstock and close to hiking trails Relax in the New hot tub on private outdoor deck reset yourself in the 2 person custom steam room also a Salt water inground pool available King size bed in loft and pull out full mattress in sectional couch just renovated with all new furniture full kitchen

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.

Upstate Getaway btw Rhinebeck+Hudson
Our home is located on an unpaved, private road in a quiet area and features an in-ground, heated, saltwater pool open between Memorial Day and Late September. In 2026, the pool will be available for bookings 5/22 - 9/18. A quiet and private getaway in the Hudson Valley and convenient to many popular activities. NOTE: For bookings during pool season, guests will be asked to review and agree to the safety rules relating to the pool.

Peaceful Light-Filled Guesthouse salt pool/sauna
Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit, or unwind in the pool side sauna. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Retreat with Heated Pool, 1 Mile to NYC Train
The pool is open for the 2026 season. Escape to a stunning 4-BR home on 2 acres in Redding, CT (#1 Small Town). Just 90 mins from NYC, this luxurious retreat comfortably fits 8 guests. Enjoy hotel-style amenities, a heated saltwater pool, and a gourmet kitchen. Breathe in fresh country air in a peaceful, park-like setting. Perfect for families, offering a blend of modern comfort and outdoor living.

Escape to a Restored New England Antique Milk Barn
A Bucolic antique farm property in the Fairfield County countryside. Welcome to Connecticut country living at its best! Enjoy the gardens from your private patio, take a dip in the pool, read a book surrounded by fall foliage and retire to your very private suite and relax in the soaking tub. Please note the owners reside on the 4 acre property but give guests the utmost privacy.

Huge eclectic space w/ private pool. 1.5hr to city
1.5 hrs from NYC; minutes driving from hiking trails; 20 min from Beacon and Cold Spring! The bottom floor of this 1865 Carriage House has been transformed into an eclectic retreat. The 2500 sq ft private apartment has a room for every mood and super unique decor in every corner! There is also a vintage/antique shop on the property— 20% off for our guests ;)
Popular amenities for New Milford rentals with a pool
House rentals with a pool

Cozy, Modern Retreat in the Woods of Cold Spring

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

Luxury Retreat with pool in historic Kingston

Hudson River views with pool and hot tub

Designers Historic Connecticut Home

Bluewater Lodge at Candlewood Lake

Hillside Oasis
Other holiday rentals with a pool

Lovely country house; stunning view

BUNTING HOUSE : CANDLEWOOD LAKEFRONT! 3BR CHALET

Classic Red Barn with game room and gym

The Pool Cottage at Narrow Valley Estate

The Dahlia Villa within Westerhall Gardens

The Perch: Saltwater Pool Woodland Cottage Retreat

Punto Pino Farm Stay

2 bedroom private suite. 2nd floor. No kitchen.
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- Waterfront rentals New Milford
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- House rentals New Milford
- Family-friendly rentals New Milford
- Rentals with a hot tub New Milford
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- Pet-friendly rentals New Milford
- Rentals with a kayak New Milford
- Rentals with pools Connecticut
- Rentals with pools United States
- Yale University
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Fairfield Beach
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Sunken Meadow State Park
- Taconic State Park
- Mohonk Preserve
- Storm King Art Center
- Bash Bish Falls State Park
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Harriman State Park
- Compo Beach
- Hammonasset Beach State Park
- Mohawk Mountain Ski Area
- Powder Ridge Mountain Park & Resort
- Storm King Art Center
- Sleeping Giant State Park
- Millbrook Vineyards & Winery
- Sherwood Island State Park
- Ski Sundown





