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Vacation rentals with outdoor seating in West Stockbridge

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Top-rated outdoor seating rentals in West Stockbridge

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

Guest favorite
Home in Lee
Cozy Berkshires Cottage
Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)
May 22 – 29
$117 per night
Guest favorite
Cottage in Great Barrington
Artist Cottage
Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.
Jun 12 – 19
$181 per night
Guest favorite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
Hello hip, glamping cabin! The decor is chic & bohemian cool! Enjoy the large yard & sunny deck. Fieldstone fireplace w/ vaulted ceilings & skylights. Cottage has beautiful pine throughout w/ fabulous interior design picks. Enjoy the sweet reading nook, master bedroom w/ skylights or put on a favorite record. Kids will love the cozy sleeping loft. A 8-10 minute walk or 2 minute drive to lake public beach (The lovely Stockbridge Bowl) Outdoor shower. BBQ grill, great outdoor space to play.
Jan 4 – 11
$399 per night

Popular amenities for West Stockbridge outdoor seating rentals

House rentals with outdoor seating

Guest favorite
Home in Great Barrington
Elegant Year-Round Lakeside Retreat with AC
Oct 11 – 18
$399 per night
Guest favorite
Home in Stockbridge
Sun-filled, Charming Stockbridge Classic- In Town!
Sep 17 – 24
$247 per night
Guest favorite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
Jun 23 – 30
$225 per night
Guest favorite
Home in New Lebanon
The old sawmill from 1771
Dec 20 – 27
$125 per night
Guest favorite
Home in Canaan
Country Cottage
Dec 14 – 21
$135 per night
Guest favorite
Home in Austerlitz
Peaceful Renovated Barn in the Berkshires
May 9 – 16
$273 per night
Guest favorite
Home in Monterey
Charming cottage w/ gorgeous views.
May 1 – 8
$145 per night
Superhost
Home in Canaan
Orchard House-HudsonValley
Jan 17 – 24
$235 per night
Superhost
Home in Lenox
Berkshire, MA Getaway! Mile to town
Apr 25 – May 2
$251 per night
Guest favorite
Home in Chatham
Pet-friendly, Chatham, NY. No neighbors in sight.
Sep 4 – 11
$180 per night
Guest favorite
Home in Chatham
2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
Nov 6 – 13
$102 per night
Guest favorite
Home in Chatham
Beautiful Lake/Mountain Views. Bright Sunlit Home.
Feb 12 – 19
$300 per night

Apartment rentals with outdoor seating

Guest favorite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
May 31 – Jun 7
$126 per night
Guest favorite
Apartment in Lenox
Station House 1E Private Room & Bath
May 9 – 16
$64 per night
Guest favorite
Apartment in Petersburg
The Beer Diviner Brewery Apartment
Jun 5 – 12
$59 per night
Guest favorite
Apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
Mar 15 – 22
$60 per night
Guest favorite
Apartment in Hillsdale
Serene Suite Catamount Berkshires Walk to Brewery
May 2 – 9
$122 per night
Guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
Oct 17 – 24
$116 per night
Guest favorite
Apartment in Ghent
Charming Ghent Getaway, minutes from Hudson!
Jun 26 – Jul 3
$94 per night
Guest favorite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
May 20 – 27
$139 per night
Guest favorite
Apartment in Lenox
Lovely Downtown Lenox apt, walk to everything!
Oct 26 – Nov 2
$275 per night
Guest favorite
Apartment in Canaan
West Main
Apr 24 – May 1
$115 per night
Guest favorite
Apartment in North Adams
See MoCA from your mansion+Sauna! Ski nearby!
Jan 18 – 25
$129 per night
Guest favorite
Apartment in Bennington
The Octopus's Garden
Mar 14 – 21
$85 per night

Condo rentals with outdoor seating

Guest favorite
Condo in Hudson
Harmony Valley Home, bright & inviting 2-BR escape
Nov 3 – 10
$124 per night
Guest favorite
Condo in Hancock
Cozy Condo @ Jiminy Peak
Aug 9 – 16
$150 per night
Guest favorite
Condo in Lenox
Spacious 3 bedroom apt in Lenox historic downtown
Jun 15 – 22
$320 per night
Guest favorite
Condo in Hancock
Upscale 2 bed/2bath Condo at a Mountain Resort!
May 10 – 17
$236 per night
Guest favorite
Condo in Hancock
Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Oct 16 – 23
$461 per night
Guest favorite
Condo in Hancock
All-season Berkshires ski resort condo - Sitzmark
May 29 – Jun 5
$175 per night
Guest favorite
Condo in Albany
Cozy luxury brownstone w/ parking & yard
Oct 29 – Nov 5
$148 per night
Guest favorite
Condo in Stillwater
Cozy hideaway
Oct 5 – 12
$240 per night
Condo in Hancock
Bentley Brook Presidents Week & Christmas
Dec 22 – 29
$379 per night
Condo in Pittsfield
Serene Retreat in the Scenic Berkshire Mountains
Nov 27 – Dec 4
$499 per night
Guest favorite
Room in Great Barrington
Quiet refuge in Great Barrington
May 31 – Jun 7
$42 per night
Guest favorite
Room in Saugerties
Hudson Valley Hiker’s Loft-Private Room Queen Bed
May 11 – 18
$57 per night

Quick stats about vacation rentals with outdoor seating in West Stockbridge

Total rentals

30 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

930 reviews

Nightly prices starting at

$170 before taxes and fees

Destinations to explore