Vacation rentals with a pool in Amherst

4.93 out of 5 average rating, 519 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

4.98 out of 5 average rating, 61 reviews

A vibrant swimming pool reflects the blue sky and fluffy clouds above. Lush green hills and colorful flowers can be seen in the background, surrounded by a rustic wooden fence, creating a serene outdoor retreat.

Home in Chesterfield

High Field Farm

Come to High Field Farm to getaway and unwind in a beautiful, classic New England farmhouse. Set on over 500 acres of land, enjoy a spacious, tasteful and pristine country vacation home, lovingly cared for by the same family for over 50 years. The house offers four bedrooms and two full bathrooms, and endless outdoor opportunities like hiking or fly-fishing. You'll enjoy spectacular mountain views in an idyllic and private country setting that will enchant and nourish your heart and soul.

5 out of 5 average rating, 144 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

4.92 out of 5 average rating, 244 reviews

Wood, sunshine & movies in best downtown location

Sun-drenched 1st fl apt in 2-family Victorian, steps from Northampton's vibrant downtown. 2 spacious queen bedrooms, 1 bedroom/study with pull-out king. Pine-paneled kitchen with breakfast bar; open living/dining room; stereo with turntable and vintage record collection; home theater with projector. Private deck. Wood floors throughout apartment. 42" HDTV in master bedroom. Hi-speed Internet. Laundry room in basement with washer/dryer (shared with upstairs apt). Shared heated pool (Mar-Nov).

4.8 out of 5 average rating, 239 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 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.

4.95 out of 5 average rating, 111 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.

4.95 out of 5 average rating, 171 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.

5 out of 5 average rating, 57 reviews

An outdoor area features a serene pool surrounded by lush greenery, flowering plants, and decorative rocks. Wooden lounge chairs are positioned nearby for relaxation, while a mix of vibrant trees provides a natural backdrop to the historic home adjacent to the pool.

Villa in Longmeadow

Comfort and Luxury - 180 year Old Gothic Estate

This 180 year old home provides luxury and comfort for up to 10 guests. Perfect for family gatherings or a group of friends wanting to get away . Chef prepared meals and house keeping services are offered at additional rates. Conveniently located only 15 miles north of Hartford/Springfield BDL Airport and a 5 minute drive to Springfield's MGM casino. PLEASE note that guest of record is required to have at least 3 Five Star reviews in order to book

4.78 out of 5 average rating, 235 reviews

A clear, inviting pool is surrounded by lush greenery and mature trees, providing a serene and private atmosphere. The pool features a gently curving shape and is bordered by textured stone paving, with sunlight reflecting off the water's surface.

Apartment in Holyoke

NE Historical Mansion-pets and pet lovers welcome

Enjoy seamless check-in and a private 1,000 sq ft space on the third floor of our historic Victorian home. Includes 2 bedrooms, bathroom, open hallway, and a combined living/dining/kitchenette area (no sink). Pet-friendly, updated, and comfortable year-round. Accessed via the back staircase; only the entry/hallway is shared. 3rd and Top floor is strictly for guests only. Just 5 min to I-91 and Pike, 15 min to Northampton 15 min to Big E.

4.95 out of 5 average rating, 44 reviews

A charming brick exterior of the retreat features multiple large windows and a welcoming front entrance. Lush green grass surrounds the property, with decorative landscaping elements visible, including flowering plants. Solar panels are situated on the roof, reflecting an eco-friendly design.

Guesthouse in Enfield

Close BDL AirPort & SixFlags Free Private Parking

Escape to Pineside Retreat in Enfield, CT—a tranquil haven blending comfort and nature. Conveniently located 20 minutes from Bradley Airport and MGM Springfield Casino, 15 minutes from Six Flags, 22 minutes from Holyoke Mall, 5 minutes from Scantic River State Park, and 10 minutes from Windsor Locks Canal State Park. Perfect for professionals or adventurers seeking relaxation in a cozy, rustic-modern retreat.

4.96 out of 5 average rating, 302 reviews

A refreshing pool is surrounded by vibrant flowers and greenery, providing a serene outdoor setting. Lounge chairs are arranged around the pool, inviting relaxation. The pool area is fenced, ensuring privacy and safety for guests.

Guest suite in Amherst

Sunlit Clean Amherst Cozy Log Cabin

Peaceful log cabin on an 8 acre property. Truly a gem to enjoy: a quiet, relaxing, cozy, sunlit cabin with a vaulted ceiling. Beautiful gardens, warm electric fireplace, and steps away from Atkins Reservoir and hiking trails. You will feel secluded but close to local attractions. Umass only 7 minutes away and close to Amherst College, Hampshire College, Smith College, and Mount Holyoke as well.

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Popular amenities for Amherst rentals with a pool

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House rentals with a pool

5 out of 5 average rating, 11 reviews

Home in Amherst

Stay in Robert Frost's beautiful house

4.8 out of 5 average rating, 5 reviews

A hot tub is positioned on a wooden deck, surrounded by several lounge chairs. The backdrop features a well-maintained yard with a fence, and a glimpse of a pool can be seen beyond. Nearby, the lush greenery of Mt. Sugarloaf is visible, under a clear blue sky.

Home in Deerfield

New place to stay

Serene South Deerfield Retreat

The Family Room features a stone fireplace with a clock above, surrounded by comfortable seating and decorative pillows. A colorful area rug anchors the space, while wall art adds character. Soft lighting from lamps creates a cozy ambiance, complemented by shelving with decorative items.

Home in Longmeadow

Luxury 2 Bedroom Basement Apt

A spacious living area includes a large sectional sofa in a muted tone, accented with red cushions. A glass coffee table is positioned centrally, while a decorative fireplace adds warmth. Two red and black chairs are placed against the wall, enhancing the inviting design.

Home in Springfield

Ezekiel's Palace 24th

5 out of 5 average rating, 41 reviews

Home in Whitingham

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

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

4.91 out of 5 average rating, 11 reviews

A two-story house features light yellow siding with blue shutters around the windows. The front yard is well-maintained, showcasing green grass and neatly trimmed bushes on either side of the entrance. A concrete driveway runs alongside the home.

Home in Enfield

3 bdrm house great neighborhood

The exterior of a motel is displayed, featuring a prominent sign at the forefront. The two-story white building is complemented by surrounding greenery and well-maintained shrubbery. A red structure is visible adjacent to the main building, providing an inviting appearance.

Home in Charlemont

4.57 out of 5 average rating, 14 reviews

The lodge

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Other vacation rentals with a pool

4.89 out of 5 average rating, 131 reviews

Home in Colrain

The 1770 House

A child relaxes on a clear inflatable float in a sparkling swimming pool. Colorful bubbles and additional floats drift nearby, while sunlight reflects brightly on the water's surface. The pool's uniform depth is visible along the sides.

4.98 out of 5 average rating, 316 reviews

Sunny Inspirit Apartment in best downtown location

4.93 out of 5 average rating, 519 reviews

Bungalow in Easthampton

The Creation Station

A child is seated on a large, silver glittery inflatable float in a bright blue pool. The water reflects sunlight, creating a playful atmosphere. Nearby, a large beach ball and another float can be seen, adding to the inviting pool scene surrounded by wooden fencing and greenery.

4.94 out of 5 average rating, 231 reviews

Light-bathed 3br w porch in best downtown location

5 out of 5 average rating, 144 reviews

Guest suite in Enfield

Luxe 1822 Apt | Rain Shower | Plush beds | Firepit

4.95 out of 5 average rating, 171 reviews

Cabin in Guilford

Silver Brook Cabin

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.

4.99 out of 5 average rating, 229 reviews

Skylights, art + design in best downtown location