Vacation rentals with a pool in Monticello

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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

Apr 3 – 10

€ 669 per night

Guest favorite

Condo in Vernon Township

4.97 out of 5 average rating, 217 reviews

Rustic Chic at Mountain Creek! Pool|Hot Tub|Sauna

From skiing, snowboarding to mountain biking, waterpark, hiking, zip lines, open year round heated pool, hot tub, sauna & more! Enjoy all that Rustic Chic at Mountain Creek has to offer! 1B/1b condo w/king bed, queen sofa bed & cozy fireplace -The perfect getaway for a couple, small group or family! Steps to Mountain Creek Ski Resort & Waterpark.* *Located in The Appalachian directly next to Mountain Creek Resort! "Comfortable, chic, super clean, and thoughtfully decorated condo."~Marianne

Nov 21 – 28

€ 182 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.

Sep 22 – 29

€ 86 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 27 – Oct 4

€ 498 per night

Guest favorite

Home in New Paltz

4.98 out of 5 average rating, 437 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

Sep 21 – 28

€ 753 per night

Guest favorite

Cabin in Albrightsville

4.94 out of 5 average rating, 135 reviews

Cozy Pocono Cabin on an Acre

If you are looking for a quiet and intimate getaway or adventure, this is it! Step into this unique log sided cabin with all the Pocono's aesthetic you could want. Relax & recharge in the open concept knotty pine kitchen and living room. The vaulted loft provides an open & airy feel. The bedrooms feature brand new beds and large closets. The kitchen is well stocked and the living room features a wood burning fire place, Roku TV, two couches, a DVD collection, Nintendo 64 and boardgames.

Sep 5 – 12

€ 146 per night

Guest favorite

Home in Woodstock

4.98 out of 5 average rating, 101 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..

Mar 15 – 22

€ 818 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.

Sep 10 – 17

€ 619 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.

Oct 21 – 28

€ 106 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

Sep 23 – 30

€ 643 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!

Jan 16 – 23

€ 316 per night

Guest favorite

Cabin in Red Hook

4.96 out of 5 average rating, 306 reviews

Modern Upstate Cabin, near Rhinebeck NY

🏊🏽‍♂️Heated pool is open. (Will be winterized mid October Welcome to Maitopia. This beautifully designed passive glass and wood modern cabin offers elegant modern details and the warmth that only an upstate energy efficient retreat could. With a soaking egg tub, fires at every turn and a heated pool you will fall in love with the place and the towns nearby.

Aug 22 – 29

€ 473 per night