A wooden boardwalk leading to a beach with a bird on the railing.

City Meadow Boardwalk Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for City Meadow Boardwalk vacation rentals

Interior

1. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is ￥34,976
￥54,902 total
includes taxes & fees
Aug 31 - Sep 1
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Terrace/patio

2. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (50 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is ￥20,068
￥34,227 total
includes taxes & fees
Aug 19 - Aug 20
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Exterior

3. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is ￥15,218
￥45,471 total
includes taxes & fees
Aug 19 - Aug 20
Cozy Attic 10 min to Llitchfield
2 bedrooms, WiFi (free), bed sheets

4. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is ￥20,800
￥37,230 total
includes taxes & fees
Aug 24 - Aug 25
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Dining

5. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is ￥22,395
￥69,150 total
includes taxes & fees
Sep 1 - Sep 2
Art House 3 Beds Close to Warner Theater
Exterior

6. Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is ￥20,570
￥53,695 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Modern Farmhouse Private Apt - 3 Beds
Smart TV, fireplace

7. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
The price is ￥24,846
￥43,425 total
includes taxes & fees
Sep 2 - Sep 3
Pristine Cozy Walkable Downtown 2BR Getaway
Beach nearby, sun loungers, beach towels

8. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is ￥32,834
￥46,824 total
includes taxes & fees
Sep 13 - Sep 14
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Coffee/tea maker, fridge, microwave, oven

9. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥43,035
￥64,806 total
includes taxes & fees
Aug 25 - Aug 26
Home in Great Barrington
Property grounds

10. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
Cheerful 3-bedroom cottage with woodstove
Dining

11. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is ￥37,269
￥82,978 total
includes taxes & fees
Aug 16 - Aug 17
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Coffee/tea maker, fridge, microwave, oven

12. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is ￥46,443
￥60,459 total
includes taxes & fees
Sep 3 - Sep 4
The Jefferson Guest House, Spacious, Special Views
1 bedroom, desk, iron/ironing board, WiFi

13. Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is ￥20,570
￥64,525 total
includes taxes & fees
Aug 17 - Aug 18
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
TV

14. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is ￥52,559
￥102,019 total
includes taxes & fees
Sep 2 - Sep 3
Treetop Hideaway in Tyringham
3 bedrooms, iron/ironing board, WiFi, bed sheets

15. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ￥66,575
￥109,412 total
includes taxes & fees
Sep 9 - Sep 10
Cozy. Clean. Free bagel shop. 3 Fireplaces.
TV, fireplace, printers

16. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥90,163
￥209,056 total
includes taxes & fees
Aug 19 - Aug 20
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Coffee/tea maker, fridge, microwave, oven

17. Renovated Downtown Great Barrington House

Renovated Downtown Great Barrington House
Great Barrington
8.0 out of 10, Very Good, (2 reviews)
"This is a very nice place to stay. My wife and I both remarked on how comfortable we felt there. A proper home away from home. It was well stocked on all fronts, including the kitchen. And I think what put the finishing touch on was the attention to detail... The towels were large, the bathroom rolls were Charmin Ultrasoft, and there were tissue boxes everywhere you're likely to need them. The hosts seem to work with a service, so you can reach someone with questions immediately, and the hosts...
United States
Anonymous traveler
The price is ￥205,912
￥323,270 total
includes taxes & fees
Aug 23 - Aug 24
Renovated Downtown Great Barrington House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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