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

Mid-century A-frame nestled amongst the trees
NEW Hot tub added! This little A-frame is a mid century dream nestled among the trees in the Pocono Mountains of Northeastern Pennsylvania and is within a few minutes walk to the lake. Beautifully and loving curated, filled with mid- century furniture, lots of art, books and records. A highlight of the cabin is the upstairs bathroom, featured in Condé Nast, Houzz and West Elm, it's a Pinterest dream come true. Come take a soak in our beautiful soaker tub among the trees. 2 hours from NYC.

Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm
This one-of-a-kind property nestled in the quiet village of North Branch has all the makings of a dream vacation. This cozy home in the woods has 3 stunning acres with creek access towards the end of the property! Enjoy a full-size heated indoor pool + an infrared sauna open year-round combined with breathtaking scenery. If you're looking for a vacation for kids + adults, this peaceful home is for you! Enjoy a relaxing vacation in a comfortable home with all the beauty that nature has to offer.

Stunning Mountain Cabin w/ Pool & Hot Tub
This designer home is in the western Catskills, 2hrs away from NYC on 10 acres of hillside property. 20 mins from the Kartrite indoor water park. Perfect family getaway for hiking, canoeing, fishing , water sports. Quiet, secluded, fully stocked kitchen, 360 degree views , patio deck seating private heated pool from May 20- Sept 30 cabana, hammock, loungers Starting March 1st 2021, we are offering our newly installed Hot Tub/ Spa ( 5-6 seater) set into the side of hill w/ magnificent views

Relaxing Wooded Retreat w amenities
This Lake House getaway sits on a serene 7 acres of private land. Perfectly positioned for adventures in Sullivan County,Ny and beyond, it is an oasis of tranquility for couples, families, and friends alike. This home is a spacious six bedroom with 10 beds an extra sleeping amenities if needed.Seasonal pool, 2 Canoes, Kayak, and indoor Sauna,Pool table , and a 6 person hot tub , hikes, great restaurants, farm stands, and fresh mountain air await. Close to holiday mt skiing & catskill casino

Design Farmhouse w/ Pool + Firepit | Hudson Valley
A private, design-forward escape in Accord. One of the Hudson Valley’s most sought-after locations. BoHo Farm House is a luxe 3BR/3BA on 8 acres with a large dog-friendly fenced area. Recently renovated and featured in PureWow, the home offers vaulted ceilings, a light-filled open living space, chef’s kitchen, cozy fireplace, fire pits, and spa-like baths. Minutes from Inness, Westwind Orchard, Arrowood, and Stone Ridge, with easy access to hiking, skiing, and top farm-to-table dining. ⸻

Experience The Zen House
Enjoy your own private indoor movie theater with 7.1 Klipsch Premiere Surround Sound and leather recliner seats, a spa with a cold plunge pool & sauna, and a hot tub to reach the maximum level of relaxation. Play a game of ping pong, enjoy the fireplace outside and inside along with 5 acres! Amenities Include: - Hot Tub - Bath House with Sauna & Cold Plunge Pool - 12 Person Theater with immersive visual & surround sound + recliners - Game Room - Outdoor Fire Pit - Hammock & much more!

6-Acre Lux Estate: Hot Tub, Fireplace, Near Skiing
A modern 3BR/2BA Catskills retreat on 6 private acres with a hot-tub, and fireplace. Perched on a hill, this single-level home offers serenity, scenic views, mid-century modern decor, and comfort—ideal for girls' trips, couples and families. Amenities: Fireplace Hot Tub Spa Mini Ping-Pong Dart Board High-speed Wi-Fi Narrowsburg Offers: -Restaurants & Shops -Luxury Spas & Yoga -Alpaca Farm -Hiking -Farmer's Markets -Delaware Valley Arts Alliance Experience the best of the Catskills!

Woodstock Historic Artist Estate- The Museum House
The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Bella Cottage w/Cozy Fireplace, Winter Getaway
Disconnect, relax and rejuvenate in this cute country home! Enjoy the serene, wooded surroundings as you watch deer trot by and end your day unwinding under starlit night skies. This 2-acre gem is tucked away on a private drive, just off the main road. Though secluded, grocery stores and restaurants are just down the street. The house is equipped with all the modern amenities to make your stay comfortable.

Spacious Catskills Farmhouse on over 5 acres!
Spring into fun in the Catskill Mountains! Enjoy a hike at one of our local trails or nature preserves. Try your luck at the casino, spend a day at the indoor water park, or play a round of golf at one of the local courses. You will feel right at home in this charming & restored 5BR farmhouse. Located on 5+ acres near the great Catskills Forest Preserve, this is a great place for four-season recreation.

Ski & Sauna! Modern Mountain Escape
Welcome to a brand new Catskills getaway. Inspired by Japanese and Scandinavian design, every detail has been thought through to create the perfect private retreat where interiors blend seamlessly with the surrounding mountains. You’ll see high end finishes throughout the space and all the amenities you could desire. Welcome to a relaxing stay at your home away from home.

Golf Sim! Hot Tub/Game Room/Cinema 2 Kings
A stay here is an experience! The perfect place for a group or multiple families. *Hot Tub *Game Rm: Poker Table, Ping Pong, Air Hockey, Basketball, Arcade, Skee Ball & Large Screen TV. *Cinema Room *2 King Bedrooms 1 Queen & 2 Bunk rooms Amenity Passes available - $10/ person/day for pools, beach & Fitness Center.
Popular amenities for Monticello rentals with a pool
House rentals with a pool

Hemlock Mntn Estate; Spacious, Indoor Hotub, POOL

Oak View: Vintage Fireplace, Sonos Sound, Firepit!

Scenic River View Escape | New Paltz

Highwoods Haven | saltwater pool and hot tub

Luxury Pocono Retreat:Jacuzzi, Sauna, Gym, Games

MODERN FARMHOUSE in the WOODS

Lake Front Retreat in the Poconos * King Bed*

Cozy & Spacious Country Home - All Seasons
Condo rentals with a pool

Lovely 1 Bedroom/Pool/Hot Tub/King Bed/Ski In/Out

206 · Renovated Chic Premium 1 bdrm

Valley Overlook @ Mtn Creek Resort Park & Play

Cozy Retreat | Pool & Hot Tub | Mountain Creek Resort @ Appalachian

Comfy Studio at Mountain Creek Resort

Appalachian Lodge Top Floor w/views

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5

1BR Mountain Front Condo at the Appalachian #324
Other vacation rentals with a pool

The Wooden Igloo Near Legoland NY

Farm House jacuzzi opens 4/10 pool opens May15

Large Private Hidden Estate! 30+ ppl, HotTub, Pool

Au Bon Orchard - Hot Tub - 56 Private Acres

Catskills Creek | Forest Views, Hot Tub & Pool

Livingston Manor Retreat

Pondview Manor - Farmhouse w/ Pool

Private Lakeside Retreat- Pool/2HotTub/Sauna/RV
Quick stats about vacation rentals with a pool in Monticello

Total vacation rentals
Explore 30 vacation rentals in Monticello

Nightly prices starting at
Monticello vacation rentals start at $623 CAD per night before taxes and fees

Verified guest reviews
Over 30 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
30 of Monticello vacation rentals include wifi access

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

4.7 Average rating
Monticello stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Mississauga Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Fitness-friendly rentals Monticello
- Rentals with a fireplace Monticello
- Pet-friendly rentals Monticello
- Resort rentals Monticello
- House rentals Monticello
- Apartment rentals Monticello
- Family-friendly rentals Monticello
- Rentals with an EV charger Monticello
- Villa rentals Monticello
- Cottage rentals Monticello
- Rentals with a patio Monticello
- Cabin rentals Monticello
- Rentals with pools Sullivan County
- Rentals with pools New York
- Rentals with pools United States
- Hunter Mountain
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Elk Mountain Ski Resort
- Bethel Woods Center for the Arts
- Bushkill Falls
- Minnewaska State Park Preserve
- Sunset Hill Shooting Range
- Resorts World Catskills
- Delaware Water Gap National Recreation Area
- Windham Mountain
- Hunter Mountain Resort
- Mount Peter Ski Area
- Plattekill Mountain
- Brotherhood, America's Oldest Winery
- Shawnee Mountain Ski Area
- Promised Land State Park
- Bear Mountain State Park
- Wawayanda State Park
- Pocono Mountains
- Opus 40
- Claws 'N' Paws
- Storm King Art Center
- Benmarl Winery




