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

City Meadow Boardwalk Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for City Meadow Boardwalk holiday rentals

A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

1. 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, (55 reviews)
"Clean property, very cute. Also very small. Cable/tv access was challenging, but all on all a good experience"
United States
traci
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is HK$902
HK$1,654 total
includes taxes & fees
2 Nov - 3 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

3. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (9 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is HK$883
HK$1,293 total
includes taxes & fees
30 Oct - 31 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
A two-story house with a front porch, a small balcony, and a white picket fence.

4. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is HK$684
HK$2,709 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Attic 10 min to Llitchfield
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

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 HK$1,123
HK$3,409 total
includes taxes & fees
2 Nov - 3 Nov
Art House 3 Beds Close to Warner Theater
A two-story house with a front porch, a small balcony, and a white picket fence.

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 HK$1,112
HK$3,355 total
includes taxes & fees
29 Oct - 30 Oct
Cozy Modern Farmhouse Private Apt - 3 Beds
A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

7. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is HK$1,257
HK$1,580 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Camper tucked into the woods
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

8. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is HK$2,856
HK$4,798 total
includes taxes & fees
11 Nov - 12 Nov
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

9. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,391
HK$3,351 total
includes taxes & fees
9 Nov - 10 Nov
Cheerful 3-bedroom cottage with woodstove
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

10. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (55 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is HK$2,001
HK$4,611 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Cottage-Sunset On The Lake
A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

11. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
10.0 out of 10, Exceptional, (1 review)
"We loved the place, which feels like your own house in the woods. The setting is gorgeous especially with the leaves changing colors. We specifically chose the location so we could bike the Farmington Trail loop which starts at the bottom of the hill. The house is so well stocked with everything you could think of, especially coffee and there is plenty of space to relax inside and out. The host was very attentive to our needs. It couldn’t have been better for us."
United States
Margaret A.
The price is HK$1,398
HK$1,765 total
includes taxes & fees
2 Nov - 3 Nov
Collinsville River Escape / Fall Foliage, Deck & Yard
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

12. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (22 reviews)
"It was great!"
United States
Amanda T.
The price is HK$1,413
HK$2,356 total
includes taxes & fees
9 Nov - 10 Nov
Pristine Cozy Walkable Downtown 2BR Getaway
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

13. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is HK$1,808
HK$2,809 total
includes taxes & fees
26 Oct - 27 Oct
Home in Great Barrington
A sandy beach with a lake and forest in the background.

14. 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, (6 reviews)
"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"
United States
Marc R.
The price is HK$1,640
HK$2,577 total
includes taxes & fees
25 Oct - 26 Oct
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A wooden wall with a large mirror, a wooden console table, and two wall-mounted lanterns.

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

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is HK$1,096
HK$3,275 total
includes taxes & fees
14 Oct - 15 Oct
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

16. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 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 HK$2,127
HK$4,421 total
includes taxes & fees
9 Nov - 10 Nov
Treetop Hideaway in Tyringham
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

17. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"
United States
genevieve
The price is HK$2,288
HK$2,940 total
includes taxes & fees
15 Oct - 16 Oct
The Jefferson Guest House, Spacious, Special Views
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is HK$3,139
HK$5,514 total
includes taxes & fees
20 Oct - 21 Oct
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

19. 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, (9 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 HK$4,464
HK$10,456 total
includes taxes & fees
14 Oct - 15 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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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