Entire home

Swim All Day. Stroll to Dinner. Repeat.

Photo gallery for Swim All Day. Stroll to Dinner. Repeat.

A rectangular swimming pool with a wooden deck and lounge chairs, surrounded by a wooden fence and trees.
A kitchen with a wooden countertop, a sink, and a dining area with a blue sofa and a wooden coffee table.
A residential driveway leading to a house with a covered porch, surrounded by lush greenery and trees.
A modern kitchen with a central island, white cabinetry, and a wooden floor.
A two-story house with a red and white exterior, surrounded by a well-maintained lawn and dense trees.

Reviews

10 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Unmatched views, unforgettable moments
    Guests like the location for the scenic views.
  • Discover nearby landmarks
    Walk to Mahaiwe Performing Arts Center

Popular amenities

  • Hot tub on site
  • Private pool
  • Patio
  • Arcade/game room
  • Electric vehicle charging point
  • Barbecue grill

Explore the area

View in a map
Great Barrington, MA
  • Place, Mahaiwe Performing Arts Center
    ‪11 min walk‬
  • Place, Housatonic River
    ‪15 min walk‬
  • Place, Housatonic River Walk
    ‪19 min walk‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪46 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Single Beds

Bedroom 5

1 Double Futon

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden

Add dates for prices

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9.8 out of 10, Exceptional, (18 reviews)
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About the area

Great Barrington

Located in Great Barrington, this holiday home is in a rural area and on a lake. Tanglewood Music Center and Great Barrington Historical Society & Museum are cultural highlights, and some of the area's attractions include Mahaiwe Performing Arts Center and Lenox Arts Center. Consider Roe Jan Brewing Co. for a night out or Berkshire Botanical Garden if you're travelling with kids. Discover the area's water adventures with power boating and fishing nearby, or enjoy the great outdoors with hiking/biking trails and rock climbing.
View more Holiday homes in Great BarringtonOpens in a new window
Map
Great Barrington, MA

What's nearby

  • Mahaiwe Performing Arts Center - 11 min walk - 1.0 km
  • Housatonic River - 15 min walk - 1.3 km
  • Housatonic River Walk - 19 min walk - 1.7 km
  • Lake Mansfield Park - 3 min drive - 1.8 km
  • Ski Butternut - 8 min drive - 8.2 km

Getting around

  • Pittsfield, MA (PSF-Pittsfield Municipal) - 34 min drive

Restaurants

  • ‪Guido’s Kitchen - ‬3 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪Café Holli - ‬16 min walk
  • ‪Dunkin' - ‬14 min walk
  • ‪Cumberland Farms - ‬18 min walk

Frequently asked questions

Does Swim All Day. Stroll to Dinner. Repeat. have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Swim All Day. Stroll to Dinner. Repeat. pet-friendly?

No, pets are not allowed at this property.

How much is parking at Swim All Day. Stroll to Dinner. Repeat.?

On-site parking is available at the property.

What time is check-in at Swim All Day. Stroll to Dinner. Repeat.?

Check-in begins at 4:00 PM.

What time is check-out at Swim All Day. Stroll to Dinner. Repeat.?

Checkout is at 10:00 AM.

Where is Swim All Day. Stroll to Dinner. Repeat. located?

This family-friendly Great Barrington holiday home is located on a lake, within 1 mi (2 km) of Mahaiwe Performing Arts Center, Housatonic River Walk and Housatonic River. Lake Mansfield Park and Great Barrington Historical Society & Museum are also within 2 miles (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 16 out of 16 reviews
Rating 8 - Good. 0 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Trip

Clean, well appointed and spacious. We enjoyed the amenities and proximity to town.
Stayed 9 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home in Great Barrington

The house was beautiful and in a great location. David (owner) was friendly and easy to deal with. We wound definitely stay here again!
Stayed 8 nights in Jun 2024
Archival

10/10 Excellent

Perfection in the Berkshires

Just the perfect home for a week in the Berkshire Mountains. The pool is simply wonderful, as is the grand porch perfect for a leisurely breakfast. Secluded but a quick walk to the wonderful New England village of Great Baarrington, the house is warm, comfortable and just right for rest, relaxation and recreation. I'd give it six stars if I could. We were sorry to leave and can't wait to return.
Stayed 7 nights in Aug 2017
Response from VrboOwner on 22 Mar 2020
Well Dan, if the house could blush I'm sure it would. Thank you so much the kind words and for coming back with your family again this summer. Kind regards, David
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relax on the porch

What a wonderful way to come home in the Berkshires! This lovely property offers comfortable beds, a fully stocked kitchen, beautifully appointed living space, charming gardens and an amazing porch to gather with the whole family. The owners thought of everything and generously offer quality bath products, soaps, etc. Conveniently located near town and a short drive to excellent hiking spots. Grab your book and hop in the hammock. Ahhhh... vacation at its finest!
Stayed 9 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Great Barrington Escape

We can’t say enough wonderful things about this home. Wonderfully comfortable, walking distance to town, walking distance to a small lake + + +. The house is beautifully decorated, neat and organized. The majestic ceiling height on the first level gives a sense of comfort and space. The bedrooms are well sized and the kitchen was impressively well laid out and made preparing meals a pleasure. And all of that pales in comparison to the front deck. A phenomenal place to have coffee, eat dinner, read a book, or do absolutely nothing. Loved it. The Logans are wonderful hosts and we would definitely stay here again.
Stayed 9 nights in Jun 2022
Response from VrboOwner on 23 Jul 2022
Thank you so much Anthony. It was a pleasure to host you and your family.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful spacious home in the Berkshires

Clean spacious home to enjoy with family and friends. Comfortable bedding. Pristine pool, amazing kitchen cooked great meals. Hopefully we can return again.
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful vacation

Wonderful family home in our favorite town!! Just the right space for our extended family to relax and spend a vacation week together with lots of swimming!!
Stayed 7 nights in Aug 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Barrington Stay

This property is large and easily accommodated our party of 5 adults and 2 small children. It is in town and an easy walk to restaurants, shops and the ice cream parlor. Although in town, the well maintained grounds are large and beautifully planted with vegetable beds available to guests. The pool is large and nicely sited. One caveat: the shallow end is about 4 feet deep which can be problematic for small children who don’t swim. The kitchen is very well equipped. The wrap around porch is wonderful for relaxing and outdoor dining. Linda
Stayed 31 nights in Jul 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our Vacation in the Berkshires

Beautiful home, great location, inviting pool!
Stayed 9 nights in Aug 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Great Barrington place!

This house was spacious, comfortable and beautiful. The pool, porch and landscaping are fabulous and were such a perfect setting for our family gathering. Even though the arts events we had planned when we rented were all cancelled (due to Covid), the house and its location offered more than enough to make up for it. The owners were a pleasure!
Stayed 14 nights in Jul 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house!

A perfect stay! We love the values of the family that lives here. It really comes through and it made us feel very much at home.
Stayed 4 nights in Jul 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Turn Of The Century Home Close To Great Barrington Village

Warm, cozy and relaxing home with a great pool and kitchen!
Stayed 6 nights in Jul 2019
Verified review

10/10 Excellent

Our third time in this lovely home; it gets better with each visit. Just perfect!

Where to start? The beautiful heated pool? The porch with views of the mountain? The wonderfully appointed home? How about the 10 minute walk to delightful Great Barrington? My wife and I enjoyed every minute of our stay. This house is ideal for a family looking to relax in the Berkshires and is one of the most special places we’ve ever stayed. 10 stars!
Stayed 7 nights in Aug 2018
Response from VrboOwner on 22 Mar 2020
Thank you so much Dan. Ten stars right back at you.
Archival

10/10 Excellent

Perfection in the Berkshires

We had a perfect stay at this wonderful home in late July. It's difficult to decide the best feature of the home -- the pool, the front porch, the easy walk into town. The town is a picture-perfect New England town with lots of great shops, galleries and restaurants. We loved relaxing in the pool after a walk into town, or just lounging on the expansive porch watching the birds or having a leisurely breakfast, cooked in the fabulous kitchen. Loved this home; can't wait to go back!
Archival

10/10 Excellent

a lovely home away from home

The house was well maintained and clean when we arrived. It had a very homey feel and the kitchen and bathrooms were extremely nice. We particularly enjoyed the large front porch and the fact that we could walk into Great Barrington. The owner was responsive to questions and called to confirm the reservation which was reassuring since there were news stories of vacation disasters soon after. We would definitely enjoy staying here again.
Archival

10/10 Excellent

Perfect Vacation Home

Beautiful and comfortable home. The kids loved the pool too! The house is in a perfect location. We would love to stay here again in the future. No complaints - all was even better than pictured/stated.
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