Holiday rentals with a pool in Pioneer Valley

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Popular amenities for Pioneer Valley rentals with a pool

House rentals with a pool

Guest favourite
Home in Otis
4.92 out of 5 average rating, 13 reviews

Berkshires Oasis Retreat: Art Meets Nature

CharlotteRating, 5 stars5 months ago
We had a lovely time with our family! We were with 2 young children and my elderly father who cannot walk well (uses a walker). The house was perfectly designed to accommodate my father and had great living areas for us to spend time together. A very cozy, warm and welcoming home (with lots of amenities!). Yael is a very friendly, responsive host. We’d gladly come back for another winter or perhaps a summer stay! Thank you Yael!
Guest favourite
Home in New Lebanon
4.98 out of 5 average rating, 60 reviews

Berkshire Mountain home views, pool, Queechy Lake

GeorgeRating, 5 stars3 months ago
The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!
Guest favourite
Home in Keene
4.93 out of 5 average rating, 211 reviews

The Brick House on Washington Street

PaulRating, 5 stars2 weeks ago
Great stay and was exactly what we needed for our entire family for a weekend wedding!
Top Guest favourite
Home in Wilmington
4.96 out of 5 average rating, 28 reviews

Family/Dog Friendly Mountain Home w/ Amenities

LouisRating, 5 stars5 days ago
Jake’s home is outstanding. The beds are very comfortable. The internet is good, The home has lots of space , a great kitchen with all amenities that we needed. Gas stove etc. The outlay was very comfortable and made for the perfect vacation. I’ve stayed at many homes in the area, Jake’s place is by far the best. We also went to the Clubhouse and used the pool and hot tub which was an added surprise.
Top Guest favourite
Home in Great Barrington
4.99 out of 5 average rating, 73 reviews

Stunning luxury home with pool

StephanieRating, 5 stars3 weeks ago
Beautiful home! Extremely clean upon arrival and excellent communication. Everything in the house was clearly labeled and directions for check-in and check-out were very clear. Sadly it rained our entire stay so we could not enjoy the pool or the beautiful backyard, but we still had a lovely stay. We hope to come back soon!
Superhost
Home in New Hartford
4.79 out of 5 average rating, 42 reviews

Mountaintop Nirvana: Lake, Pool, Hot Tub, Nature

ColleenRating, 5 stars3 weeks ago
We had an amazing stay! David was quick to respond with any questions I had and even came out to hook up the propane tank for the heated pool. I saw in previous reviews about the tricky driveway but David’s description of it is perfectly accurate and not any trouble, just a little steep but nothing super tricky to deal with! The house has a beautiful setup and view, very clean and so much space. Even though it was cold and rainy we had the most fun and peaceful stay at this home. The bride of the bachelorette group said she wants to book with David on her own just for another stay/get-a-way! Highly recommend this beautiful space!
Top Guest favourite
Home in Lanesborough
5 out of 5 average rating, 22 reviews

Mountain Blossom Retreat by Evergreen Home

AlysonRating, 5 stars3 weeks ago
We selected this amazing property as the location for our mini-wedding and we could not have been happier. The house is brilliant in every way. The floor plan, the furnishings, the decor, and the grounds are all thoughtful and stunningly beautiful. The property manager was always responsive and kind. This is truly a top property and you will not be disappointed. We cannot wait to visit again.
Guest favourite
Home in Williamstown
4.89 out of 5 average rating, 218 reviews

Hollywood Bungalow in the Berkshires #C0191633410

JohnRating, 5 stars4 months ago
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

Condo rentals with a pool

Guest favourite
Condo in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars3 months ago
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.
Guest favourite
Condo in Dover
4.91 out of 5 average rating, 110 reviews

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim

MichaelRating, 5 stars3 months ago
We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.
Guest favourite
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars2 months ago
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.
Top Guest favourite
Condo in Dover
4.99 out of 5 average rating, 120 reviews

Summer Dream! The Handle Lodge at Snowtree Condos

MarkRating, 5 stars3 months ago
Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.
Guest favourite
Condo in Dover
4.95 out of 5 average rating, 61 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

BrianRating, 5 stars1 week ago
Christine was a great host. The condo was as described. The place was clean and well organized, very cute and cozy. Christine was very responsive and helpful. I will definitely stay here again.
Guest favourite
Condo in Dover
4.84 out of 5 average rating, 119 reviews

Walk to Mt. Snow-Spa-Summer Pool

GaryRating, 5 stars2 months ago
Great little studio spot to use as your Basecamp for activities in the area!
Guest favourite
Condo in Hancock
4.92 out of 5 average rating, 66 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

ArielRating, 5 stars1 week ago
We stayed at Renee’s place during a summer festival weekend hosted at the mountain and it was perfect for our needs! Comfy bed, good kitchen set up and a nice place for lounging in between festival events. Would definitely stay here again!
Superhost
Condo in Dover
4.8 out of 5 average rating, 110 reviews

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck

BrendanRating, 5 stars3 months ago
Perfect location to mt snow.. right across the street. It's an older complex but had everything we needed for a few days of skiing.. would rent again

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