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.

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Guest favorite

Cabin in Livingston Manor

4.96 out of 5 average rating, 257 reviews

Experience The Zen House

Enjoy your own private indoor HD movie theater with 5.1 Bose Surround Sound and leather recliner seats, a spa with a cold plunge pool and 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! Here are some of the key amenities: -Hot Tub (2021) -Sauna & Cold Plunge Pool -Private 12 Person Movie Theater (you can plug in your device) -Table Tennis/Ping Pong and much more! Check us out on ig: @zenhouseny

Mar 31 – Apr 7

G$135,430 GYD per night

Guest favorite

Home in Downsville

4.97 out of 5 average rating, 110 reviews

Trout fishing on the Delaware

Beautiful Private area 2 homes on 10 acres, you will have one, newly built with all amenities, on the river, great fishing, luxurious accommodations, fire stove, local town full size pool with full access, pond / beach with boating, local Knack/ Canoe rental on the East branch of the Delaware River all within 20 minuets. Local antique shops, fairs and markets, Enjoy the Catskills Today. The property boarders the River Just a walk Away. Great for Family and Children. Local food, Shopping and fun

Jan 6 – 13

G$31,702 GYD per night

Guest favorite

Cabin in Swan Lake

4.82 out of 5 average rating, 182 reviews

Stunning Sullivan County Cabin w/HotTub/Spa &Pool

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

Sep 10 – 17

G$140,379 GYD per night

Guest favorite

Condo in Windham

4.89 out of 5 average rating, 133 reviews

Cozy Mountain hideaway Windham, Hunter

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Aug 23 – 30

G$18,500 GYD per night

Guest favorite

Home in Narrowsburg

4.97 out of 5 average rating, 141 reviews

Modern Ranch With Pool & Hot-Tub

Stylish single level house with a pool- perfect for those who appreciate a good mix of comfort and sophistication while also enjoying nature. Get a buzz on while soaking in the hot tub in a spa-like setting, play a game of darts or ping-pong, or sit by the fireplace and admire the gorgeous views. Plenty to do for kids of all ages. 5 min drive to Narrowsburg Main Street restaurants and shops. Year-round farmers market close by. We put our guests’ needs at the top priority 100% of the time.

Sep 2 – 9

G$101,878 GYD per night

Guest favorite

Home in New Paltz

4.98 out of 5 average rating, 436 reviews

midcentury modern in ground pool walk 2 trail/town

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail Water St. mkt & the ❤️ of New Paltz Village. Several outdoor seating areas. The whole place is yours FULL PRIVATE ACCESS TO HOUSE/PROPERTY POOL OPEN MAY 1 - end of SEPTEMBER

Jul 14 – 21

G$191,418 GYD per night

Guest favorite

Home in Woodstock

4.98 out of 5 average rating, 100 reviews

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..

Dec 27 – Jan 3

G$238,351 GYD per night

Guest favorite

Home in Kerhonkson

4.94 out of 5 average rating, 325 reviews

Country House: Rustic Charm With Modern Feel

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

Aug 26 – Sep 2

G$185,834 GYD per night

Guest favorite

Guesthouse in Margaretville

4.99 out of 5 average rating, 134 reviews

Sunny Arts & Crafts Loft

Catskill Mtn. Summer: hiking, swimming, relaxing. Explore fun towns like Margaretville, Andes & more. May & June are almost fully booked, but lots of great summer and fall dates available. Situated on a peaceful mountainside, the loft is a cozy, private place to unwind as you enjoy a Catskill Mtn. adventure. Super savings on longer stays, too! Our road is plowed & sanded, but you will definitely need AWD & good tires to ensure smooth travels in the WINTER months.

Nov 20 – 27

G$21,259 GYD per night

Guest favorite

Chalet in Olivebridge

4.98 out of 5 average rating, 124 reviews

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

Secluded log home on 5 acres, beautifully situated at the top of a no outlet road on a mountainside in the Catskills. The home has 4 bedrooms + 3.5 baths, with the 4th bedroom being a finished basement that has built-in full size bunk beds. There is also a sunroom, screened porch, pool, hot tub, and a treehouse that resembles a floating pirate ship 30 feet up in the trees. Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

May 14 – 21

G$86,376 GYD per night

Guest favorite

Tiny home in Cochecton

4.94 out of 5 average rating, 306 reviews

Country Tiny House with Swimming Pool

Come and relax at our Tiny House Cabin by a charming creek! Our home is available for guest! We include use of swimming pool and BBQ grill..but not limited to just that! There is a comfortable bedroom with rustic alluring decor. Hot water and shower and full Kitchen to meet your needs. This is a rustic small cabin suitable for city escape. Come and enjoy our home away from the hustle . The area is within walking distance to the Delaware!

Feb 16 – 23

G$68,030 GYD per night

Guest favorite

Loft in Cornwall

4.86 out of 5 average rating, 394 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside 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 flat screen Roku TV with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have their own parking space, a private first-floor entrance, full bathroom, patio, BBQ and fire pit!

Apr 15 – 22

G$19,047 GYD per night