Wooden boardwalk crossing marshland and leading to the beach at Silver Sands State Park in Milford, Connecticut, with Charles Island visible in the background.

City Meadow Boardwalk Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for City Meadow Boardwalk vacation rentals

TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is ￥51,455
￥101,103 total
includes taxes & fees
Jun 22 - Jun 23
Treetop Hideaway in Tyringham
Smart TV, fireplace

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.
Pristine Cozy Walkable Downtown 2BR Getaway
Terrace/patio

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
9.2 out of 10, Wonderful, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is ￥25,405
￥40,024 total
includes taxes & fees
Jul 2 - Jul 3
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Dining

Whispering Estate Guest House - Countryside Getaway

Whispering Estate Guest House - Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is ￥87,102
￥142,186 total
includes taxes & fees
Jun 22 - Jun 23
Whispering Estate Guest House - Countryside Getaway
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is ￥64,520
￥111,347 total
includes taxes & fees
Jun 22 - Jun 23
Guesthouse Cabin vacation rentals in Berkshire County
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveler
The price is ￥38,470
￥59,186 total
includes taxes & fees
Jun 22 - Jun 23
Home in Great Barrington
TV, fireplace, printers

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, (6 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 ￥91,312
￥214,244 total
includes taxes & fees
Jun 22 - Jun 23
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is ￥42,099
￥64,141 total
includes taxes & fees
Jun 23 - Jun 24
Litchfield Retreat, Wineries, Foliage & Skiing
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"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 ￥48,753
￥86,349 total
includes taxes & fees
Jun 22 - Jun 23
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Dining

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 ￥34,460
￥82,694 total
includes taxes & fees
Jul 8 - Jul 9
Art House 3 Beds Close to Warner Theater
Property grounds

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.
The price is ￥38,228
￥81,258 total
includes taxes & fees
Jun 28 - Jun 29
Cheerful 3-bedroom cottage with woodstove
Fridge, microwave, oven, stovetop

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 ￥47,035
￥60,907 total
includes taxes & fees
Jun 24 - Jun 25
The Jefferson Guest House, Spacious, Special Views
Exterior

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 ￥25,574
￥69,973 total
includes taxes & fees
Jul 8 - Jul 9
Cozy Modern Farmhouse Private Apt - 3 Beds
Dining

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 ￥45,461
￥98,669 total
includes taxes & fees
Jul 7 - Jul 8
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
TV, stereo, offices

Perfect Nature Haven In Great Barrington

Perfect Nature Haven In Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (8 reviews)
"Their place was one of the cleanest rental cabins we have ever been, the house is in a great location with beautiful surroundings, the check in and check out was extremely easy for a family with little kids, loved the place and we hope to be back!"
United States
Ethel B.
The price is ￥166,946
￥315,663 total
includes taxes & fees
Jul 5 - Jul 6
Perfect Nature Haven In Great Barrington
Exterior

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.2 out of 10, Wonderful, (5 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 ￥13,549
￥42,983 total
includes taxes & fees
Jun 23 - Jun 24
Cozy Attic 10 min to Llitchfield
1 bedroom, desk, iron/ironing board, WiFi

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is ￥22,356
￥65,746 total
includes taxes & fees
Jul 8 - Jul 9
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
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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Top City Meadow Boardwalk Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Comfortable place; terrific bed; no flaws."
Alan 1-night trip
Posted 7 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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