
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

Kapitan’s Cottage Private Upstate Winter Retreat
A vintage rustic country retreat with two floors with modern amenities. 2BR, full & half bathroom. Family & Pet friendly. Large yard surrounded by a mature tree line for secluded privacy. Private stone deck w/ fire pit, BBQ & comfortable deck furniture. Summer Pool access and Generator on site. Close to Kingston, High Falls, Stone Ridge and Woodstock yet just far enough out to feel you're away from city hustle and bustle. Close to miles of hiking, outdoor activities, parks & Ski slopes.

Family Fun Getaway w/Pool/Hot tub Canoe
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

Romantic Log Cabin W/ Hot Tub, Fire Pit, Projector
Immerse yourselves in the perfect blend of serenity and romance at our fully renovated Poconos log cabin. It offers a private feel, while located in a safe neighborhood. Cuddle up in our living room day bed while enjoying backyard forest views through the giant picture window. Relax in the hot tub or by the fire pit where memories are made! Centrally located, the cabin provides access to ski resorts and hiking trails. As guests, you'll also enjoy access to the lake, pool, and sports courts.

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!

Creek Front, Hot Tub, Fireplace, & Amenities
BUSHKILL Area; On Saw Creek! Enjoy the soothing sounds of the river, relax your muscles in the hot tub room overlooking a woody lot, relax by the crackling fireplace, have a bonfire, dream away in the hammock next to the creek, and cook your favorite meals (BBQ and Convection). Enjoy the zen lounge areas in the house - loft and great room. Check out Bushkill Falls, Zip Lines, Skiing, and Rafting close by. In summer, WALK to the resort pool and tennis courts. (Lehman Rental Permit# 190089-R)

4Br l Fire-pit l Hot Tub l 10 min to Belleayre
7 min drive to Phoenicia 10 min drive to Belleayre 25 min drive to Hunter 35 min drive to Windham Renovated 1920’s cabin style home nestled on 4 acres in the Catskill Mountains. Easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, and swimming holes. A ton of outdoor space to enjoy in addition to our fully private seasonal pool (Late May-Sept). 6 person hot tub is available year round. Not for parties!! Please be mindful of our neighbors!

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!

15 mins from skiing - secluded cabin with hot tub
This 3 acre hidden gem is tucked away in the woods of the Catskills. It's a wonderful getaway from the city or any bustling lifestyle. The outdoor fire pit and hot tub are both the perfect settings for serenity. When you come up here you can enjoy hiking, leaf peeping, cooking, swimming or simply lounging & listening to our record collection and watching nature exist around you. Our house is about 20 minutes from Big Bear mountain which is a great (small) mountain for skiing and tubing.

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..
Popular amenities for Monticello rentals with a pool
House rentals with a pool

Oak View: Vintage Fireplace, Sonos Sound, Firepit!

Spacious Catskills Retreat, 5 Acres, GameRoom

midcentury mod * HOT TUB * walk out trail 2 mohonk

Entire Home (private pool), Event Friendly

Scenic River View Escape | New Paltz

Modern Lux 5-Bed, Double Fireplace, Dogs Welcome

Lake Front Retreat in the Poconos * King Bed*

Private Game house-Basketball*Hot Tub*Jacuzzi*Gym
Condo rentals with a pool

Condo at Mtn Crk 1 Bdr 1 Bath sleep 4 Mtn view 234

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

Modern Ski in/out/waterpark/King Bed/WIFI/Parking

Resort Getaway @ Mtn. Creek -pool/hot tub/sauna
Other vacation rentals with a pool

Spa & Sauna Cozy Four Seasons Retreat- 25% Off Ski

Au Bon Orchard - Hot Tub - 56 Private Acres

Livingston Manor Retreat

Spacious lodge w/ indoor pool!

The Lodge | Grateful Woods Retreat w/ HT, FP, Farm

Cheerful 3-bedroom Cabin in the Woods with a pool.

Amazing Cabin Retreat - Hot Tub, Arcade, 45 Acres!

Garden Villa | Hot Tub + Holidays + Fire Pit
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 ﺩ.ﺇ1,065 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 & kid-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
30 of Monticello vacation rentals include wi-fi access

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

4.6 Average rating
Monticello stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Boston Vacation rentals
- Greater Toronto Area Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Mississauga Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Resort rentals Monticello
- Rentals with a patio Monticello
- Fitness-friendly rentals Monticello
- Family-friendly rentals Monticello
- House rentals Monticello
- Pet-friendly rentals Monticello
- Rentals with a fireplace Monticello
- Rentals with an EV charger Monticello
- Villa rentals Monticello
- Apartment rentals Monticello
- Cottage rentals 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
- Bethel Woods Center for the Arts
- Bushkill Falls
- Elk Mountain Ski Resort
- Minnewaska State Park Preserve
- Delaware Water Gap National Recreation Area
- Resorts World Catskills
- Windham Mountain
- Sunset Hill Shooting Range
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Ringwood State Park
- Promised Land State Park
- Campgaw Mountain Ski Area
- Mount Peter Ski Area
- Wawayanda State Park
- Hunter Mountain Resort
- Plattekill Mountain
- Sterling Forest State Park
- Claws 'N' Paws
- Opus 40
- Tobyhanna State Park




