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

Bungalow in Easthampton

4.92 out of 5 average rating, 506 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

Home in Chesterfield

4.98 out of 5 average rating, 59 reviews

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.

Guest favourite

Apartment in Northampton

4.9 out of 5 average rating, 194 reviews

Luxury w sunny balcony in best downtown location

Bright, newly renovated, luxuriously furnished, tree-lined flat a few steps from Northampton's vibrant downtown. Sliding glass doors open to a lovely balcony overlooking trees and roofs. Open floor plan, eat-in butcher-block kitchen, dishwasher, living room with movie projector, home theater system, queen pullout sofa. Spacious queen bedroom with 42" HDTV, private study nook. Access to yard areas with outdoor dining table, heated 36-ft pool, play gym. Basement washer/dryer. Off-street parking.

Top Guest favourite

Guest suite in Enfield

5 out of 5 average rating, 138 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

Guest favourite

Home in Colrain

4.9 out of 5 average rating, 130 reviews

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.

Guest favourite

Home in Williamstown

4.89 out of 5 average rating, 220 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

Barn in Bloomfield

4.98 out of 5 average rating, 122 reviews

Mountaintop Horse Farm with Pool

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

Cabin in Guilford

4.95 out of 5 average rating, 170 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

Guesthouse in Lenox

4.93 out of 5 average rating, 376 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Guest favourite

Guesthouse in Williamstown

4.93 out of 5 average rating, 241 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.

Top Guest favourite

Guest suite in Amherst

4.96 out of 5 average rating, 299 reviews

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.

Top Guest favourite

Apartment in Enfield

4.99 out of 5 average rating, 242 reviews

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.