Vacation rentals with a pool in Amherst

4.93 out of 5 average rating, 513 reviews

A circular pool is set within a grassy area, surrounded by lush greenery. A shaded picnic area features a large table beneath a white umbrella. Colorful inflatables are visible on the water's surface, adding a playful touch to the serene outdoor setting.

Bungalow in Easthampton

The Creation Station

Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

4.99 out of 5 average rating, 224 reviews

A child relaxes in a transparent inflatable float adorned with glitter, gently drifting in the clear, blue waters of a heated swimming pool. Colorful pool toys are visible nearby, creating a lively atmosphere. The pool's clean lines extend into the distance, bordered by light-colored tiles.

Apartment in Northampton

Skylights, art + design in best downtown location

Elegant spacious sun-drenched 2-bdrm penthouse in 4-family Victorian on tree-lined street in downtown Northampton. Easy walk to Smith campus. Skylights; large tiled bathroom w/ shower, jacuzzi tub, washer/dryer; renovated kitchen with Italian-tiled floor; open floor plan with ample dining area; living area with large leather couch, handmade rustic wood coffee table, lg TV, Yamaha digital piano, cathedral ceiling, and glass doors onto a balcony. Home theatre in master bedroom. Off-street parking.

5 out of 5 average rating, 141 reviews

Guest suite in Enfield

Luxe 1822 Apt | Rain Shower | Plush beds | Firepit

Oversized 1800sf apartment is a 2-story unit, front half of a 200-year-old former schoolhouse in Enfield's historic district. The antique colonial is set up as a side-by-side duplex with private apartment occupying the front 1/2 of house & the owner's unit in the back with a separate driveway entrance & door. EXTRAS: ❋ PRIVATE USE OF POOL & PATIO ❋ KEYCODE CHECK-IN ANYTIME ❋ COFFEE/TEA BAR WITH EVERYTHING NEEDED ❋ POPCORN MACHINE, SNACKS & DRINKS ❋ 4 TVs: YOUTUBE TV, MAX, NETFLIX, WIFI

4.84 out of 5 average rating, 171 reviews

The Vermont Barn (Mount Snow)

Follow/Tag us on Instagram: thevermontbarn Perfect place to kick back after a long day of hiking, skiing or even just the hustle and bustle of everyday life any time of year! Enjoy our wood stove or soak in the hot tub outside. Our place is very accessible to: hiking, skiing, (Mt. Snow), kayaking, fishing, lake, biking, golfing and small town gems just down the road. Full access to Clubhouse (5 min walk): pools, hot tub, arcade and gym. Great for families, large groups, kid and pet friendly.

The outdoor pool is surrounded by a chain-link fence and features a concrete deck. Sun lounges and chairs are positioned nearby, with a colorful beach towel draped over a lounge chair. Lush greenery frames the area, providing a serene setting.

4.87 out of 5 average rating, 175 reviews

Adams Farm-"The Little Farmhouse"

A Clean Ranch style home with hardwood floors located on a 100-acre Historic Vermont Farm. Retired farmers live in separate farmhouse & are available throughout your stay. Conveniently located just minutes away from MT Snow Ski Resort, Hermitage Resort, Stratton Mt. for Skiing, Snowboarding, Tubing, Hiking & Mountain Biking. 3 miles from downtown Wilmington. Minutes to public beaches and lakes. Use our trails for snowshoeing, X-Country Skiing or hiking. Our Pool is avail July -Labor day

4.8 out of 5 average rating, 235 reviews

A spacious outdoor area features a rectangular pool bordered by a wooden fence. A pool slide extends into the water, while lounge chairs and pool equipment are arranged around the deck, all set against a backdrop of a two-story cabin with large windows. Snow gently blankets the ground.

Home in South Deerfield

Perfectly Polished Deerfield Home 5 min to I-91

A perfectly polished home, nestled in the Sugarloaf Mountain Range with a view of Mount Toby! This property offers 4 bedrooms and 4 beds. With over 2000 sqft of living space, you will enjoy coming home to wind down after a day at Yankee Candle, hiking, or other event in the beautiful Pioneer Valley. The house has something for everyone, whether it’s streaming your favorite show on Netflix, Hulu or Prime Video or relaxing on the patio deck while the kids enjoy the huge pool and water slide!

4.89 out of 5 average rating, 131 reviews

Home in Colrain

The 1770 House

Come and enjoy our country retreat with breathtaking mountain and valley views. This expanded 1770 farmhouse gives you 4,500 sq. ft. of space for large family and friend get togethers. The house overlooks the Green River Valley with views to Vermont. The end of a dirt road location provides an escape with views that are changing through the seasons. There are six bedrooms and three bathrooms. Have an event or special gathering from wedding to retirement let us know maybe we can help.

4.91 out of 5 average rating, 142 reviews

A spacious living area features large windows that allow natural light to fill the room, highlighting a stone fireplace and wooden accents. A comfortable sofa is arranged near a coffee table, with a dining area visible in the background, creating a cozy gathering space.

Cabin in Wilmington

Chic Chalet | Hot Tub · Clubhouse · Mt. Snow

Escape to The Sugar Maple Chalet, your stylish family retreat in the heart of Wilmington, Vermont. This thoughtfully updated four-bedroom home blends cozy charm with modern comforts—think high-speed Wi-Fi, a private outdoor hot tub, and a fun-filled basement bar and game room. Just a few minutes from local shops, restaurants, ski slopes, and scenic hiking trails. One well-behaved pet is welcome to join the adventure! AC installed when temperatures average above 78 degrees.

4.89 out of 5 average rating, 220 reviews

The pool area is framed by lush greenery, featuring a large in-ground pool with a slide. A colorful inflatable float is seen in the water. A shaded patio table with chairs provides a space for relaxation, alongside a sun umbrella that casts shade over the area.

Home in Williamstown

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

4.96 out of 5 average rating, 103 reviews

A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.

Apartment in Otis

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.

4.9 out of 5 average rating, 149 reviews

Martin Ski Barn - 4BR Ski House, 15 min to Mt Snow

15 min to Mount Snow, 35 to Stratton! Come enjoy our 4 bedroom, 2 bathroom home in the charming Chimney Hill area of Wilmington, VT. This home is a perfect getaway for those looking for easy living, rest, relaxation, and family fun. The house has 4 bedrooms and comfortably sleeps 8 adults. Master bedroom has a King bed, and there is one Queen room, one Full room with a twin trundle, and one room with two Twin beds. There is also a pack n’ play available for use.

4.95 out of 5 average rating, 170 reviews

A charming red cabin is nestled among lush green trees, surrounded by moss-covered ground. The exterior features multiple windows, allowing natural light to fill the space. A small shed is visible to the left of the cabin, enhancing the serene woodland setting.

Cabin in Guilford

Silver Brook Cabin

Waterfront setting in a relaxing, but convenient, location in southeastern Vermont. Photos and captions do the best job of describing our cabin, adjacent brook, and very nearby Green River with its covered bridge and swimming holes. The cabin is 20 minutes from Brattleboro with its many restaurants, shops, movie theater, and galleries. Not only is the immediate area wonderful for swimming, biking, and hiking, you can also simply relax with a good book or two.

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Popular amenities for Amherst rentals with a pool

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Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.8 out of 5 average rating, 50 reviews

A spacious kitchen is showcased, featuring warm wooden cabinets and a large central island with bar seating. Stainless steel appliances are visible, and ample countertop space accommodates preparation needs. Warm lighting creates a well-lit environment, enhancing functionality for cooking and gathering.

Home in Tolland

Peaceful Estate Getaway

4.92 out of 5 average rating, 13 reviews

A fenced outdoor area features a serene pool surrounded by lush greenery, with a gazebo nearby. A decorative sculpture adds an artistic touch, and several outdoor chairs provide spaces for relaxation. A pathway leads to the pool area, enhancing accessibility.

Home in Otis

Berkshires Oasis Retreat: Art Meets Nature

A fire pit surrounded by five green chairs is situated on a grassy area. In the background, a two-story home is nestled among trees, showcasing a porch that leads to the entrance. Natural greenery adds a serene touch to the outdoor space.

5 out of 5 average rating, 11 reviews

Modern 4BR Cabin, Near Lake & Mt. Snow

5 out of 5 average rating, 31 reviews

This living area features a stone fireplace as a focal point alongside large skylights allowing natural light to fill the space. A cozy seating arrangement is present, complemented by a patterned area rug. Large glass doors open to an accessible outdoor deck, enhancing the connection to nature.

Home in Westhampton

Happy Valley getaway

An outdoor pool is surrounded by a spacious deck, featuring numerous lounge chairs. A children's playground is visible nearby, nestled among trees and greenery. The scene captures a serene atmosphere, ideal for relaxation and family enjoyment.

4.97 out of 5 average rating, 31 reviews

Family/Dog Friendly Mountain Home w/ Amenities

4.86 out of 5 average rating, 37 reviews

The exterior of a charming house is showcased, set back from a grassy lawn. Surrounded by mature trees, the home features a peaked roof and traditional shutters, with warm light visible through the windows, indicating a welcoming atmosphere. A pathway leads to the front entrance.

Home in Amherst

Sweet cape near U Mass

An outdoor pool area features a large swimming pool surrounded by spacious concrete decking. Several lounge chairs are arranged neatly along the perimeter. Adjacent to the pool, a children's play structure is visible, set against a backdrop of green trees.

4.79 out of 5 average rating, 57 reviews

Chimney Hill Home w/ New Hot Tub & Amenity Center!