Holiday rentals with a pool in Pioneer Valley

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Top-rated rentals with a pool in Pioneer Valley

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
A charming property is illuminated with colorful lights during the evening. The spacious deck is adorned with festive decorations, and a Christmas tree can be seen through large windows. The surrounding area is dark, emphasizing the warm glow of the lights.
Bungalow in Easthampton
4.93 out of 5 average rating, 559 reviews

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

Top guest favourite
A bright and airy living space features a vaulted ceiling with a mounted ceiling fan. Large glass doors open to a balcony, framed by orange curtains. A rustic wooden coffee table sits at the center, surrounded by a leather couch and armchair, with a TV and bookshelf visible.
Flat in Northampton
4.98 out of 5 average rating, 266 reviews

1880s skylit design apt w balcony, best 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.

Guest favourite
Home in Colrain
4.89 out of 5 average rating, 138 reviews

The 1770 House

Spring is the most dramatic time here. At the end of a dirt road with no cars or people you are one with nature. Ask to see if the pool and outdoor spa are open. In March and April our rates are discounted 20%. 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 of Vermont. There are six bedrooms and three bathrooms.

Top guest favourite
A light-filled living area features a cozy sofa and elegant chairs arranged around a delicate coffee table. A decorative fireplace serves as a focal point, complemented by soft curtains and a tasteful chandelier. An ornate mirror reflects the natural light streaming through the large windows.
Guest suite in Enfield
5 out of 5 average rating, 171 reviews

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

Top guest favourite
A bright and open living space features high wooden ceilings and natural wood walls. Two chairs are positioned around a small table, with large windows allowing ample sunlight. A staircase leads to the loft area, while bookshelves and decorative plants enhance the inviting ambiance.
Home in Amherst
4.98 out of 5 average rating, 44 reviews

Calm Post+Beam Retreat

Escape into our airy, light-filled, modern, cabin. Built with wood milled right here, this serene retreat has lovely sunset views. 700 sqf detached cabin. Sleeping + office loft, 2nd queen sleeper, wood-burning stove, digital thermostat, wifi, 55” TV with Netflix, ample parking. Summer dips in the pool. North Amherst is 10 min from Amherst center, UMASS, Amherst College; 27 min to Smith College. **To access the 2nd floor office, you need to step over a beam. 1-step to the front door.

Guest favourite
A spacious living area is highlighted by a curved sectional sofa facing a media console, featuring a variety of television options. Large windows invite natural light, while warm wooden beams add structural interest to the ceiling.
Home in Deerfield
4.81 out of 5 average rating, 254 reviews

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!

Top guest favourite
A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.
Home in Williamstown
4.9 out of 5 average rating, 231 reviews

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.

Top guest favourite
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.
Flat in Otis
4.96 out of 5 average rating, 122 reviews

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.

Top guest favourite
A large farmhouse is depicted in the background, featuring a broad balcony and distinctive architectural details. Sunflowers are prominently featured in the foreground, with bright yellow petals and green leaves, surrounded by lush grass and trees providing a serene atmosphere.
Barn in Bloomfield
4.97 out of 5 average rating, 134 reviews

Farm Stay with Horses & Pool | Mountaintop Views

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Bask in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

Guest favourite
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
4.95 out of 5 average rating, 180 reviews

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.

Guest favourite
Home in Becket
4.88 out of 5 average rating, 108 reviews

Quintessential 6-BR Berkshires Lodge

Retreat to the beauty of the Berkshires in this stunning, newly renovated lodge with a brand new pool! Features vaulted ceilings, a full kitchen, hot tub, fire pit, ample yard space, dedicated study with twin bed in the atrium, and spacious basement with ping pong table. Room for families, friends, and groups to serve as their home base in the Berkshires. 5 min to Jacob's Pillow and 25 min to Tanglewood. Enjoy swimming and walks in the Becket Woods neighborhood!

Guest favourite
A serene pool area features a large in-ground pool surrounded by lush greenery. Several lounge chairs, including two green loungers and a round table with chairs, are situated on the patio. A bright red umbrella provides shaded seating, adding to the inviting outdoor space.
Guest house in Williamstown
4.93 out of 5 average rating, 256 reviews

Perfect Base for Your Berkshire Adventure

Charming private guesthouse with shared pool use. Newly renovated, the space features high ceilings, queen sized bed, rustic Arts & Crafts furniture, heat/air conditioning, and kitchenette. Located in an outbuilding on the property, the guesthouse is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3 - 5.

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