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

Reviews

10 out of 10
Exceptional
Perched on the lake, this vacation home features 4 bedrooms and 2 bathrooms, accommodating 8 guests. It includes 1 outdoor pool and 1 hot tub. Enjoy outdoor activities like motorboating and mountain climbing, while the patio provides a perfect spot to unwind. Nearby attractions include the Mahaiwe Performing Arts Center and Housatonic River.

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
4 bedrooms2+ bathroomsSleeps 8

Popular amenities

  • Private pool
  • Hot tub on site
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning

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, Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪39 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

About this property

Swim All Day. Stroll to Dinner. Repeat.

Bring the family, we've got the pool, the hot tub, and the table. Plenty of room to cook, or not, as it's a short stroll into town and all the restaurants.
Restored to its 1892 grandeur with high-end appliances and fixtures. Well maintained lawn and gardens. The home sits on 1.4 acres so although in town, it feels private. Huge wrap around porch, hammocks, charcoal and propane grill. 472Mbps internet. Apple tv, Steam shower, Peloton. Multiple areas to work including an adjustable height standing desk. Tesla Gen 3 (11.5kW output) charger.
Short walk to Lake Mansfield, restaurants, stores.
Linens are cleaned with Fragrance Free TruEarth eco-stripes. Non-toxic household cleaning products. No pets.

The Hill is the residential area just above Main St in Great Barrington voted Best Small Town in America by Smithsonian Magazine April 2012. "Big-city smart meets New England natural in an art-rich mountain setting"

Thank you for looking!
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number C0158851130
Property # 7888741
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

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 and rock climbing.
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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

  • ‪McDonald's - ‬5 min drive
  • ‪Guido’s Kitchen - ‬3 min drive
  • ‪Marketplace Kitchen Table - ‬4 min drive
  • ‪Dunkin' - ‬14 min walk
  • ‪Café Holli - ‬16 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.

How much does it cost to stay at Swim All Day. Stroll to Dinner. Repeat.?

As of 28 Aug 2026, prices found for a 1-night stay for 2 adults at Swim All Day. Stroll to Dinner. Repeat. on 1 Jul 2027 start from £8,734, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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).

About the host

Hosted by David Logan

Host profile image
Enthusiastic parent. Agreeable husband. Aspiring builder of treehouses.

Why they chose this property

In-town. Pool. Hot Tub.

What makes this property unique

In town with a pool and it's private

Languages:

English
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