Holiday Homes in City Meadow Boardwalk

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in City Meadow Boardwalk

Spacious Home nestled along the Blackberry River in Northwest CT
Fridge, microwave, oven, stovetop

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"The team stayed here for a curling tournament. Great location for that and perfect for 4 non-couple guests"
Spacious Home nestled along the Blackberry River in Northwest CT
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Terrace/patio

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay in Great Barrington for the long holiday weekend. The house is very comfortable, super clean, and the property is lovely. We were able to cool off in the pool and enjoy time with family. 10/10!"
Spectacular views and close to Great Barrington.
Relax or be active! The choice is yours in this pet-friendly family home.
Fridge, microwave, oven, stovetop

Relax or be active! The choice is yours in this pet-friendly family home.

10.0 out of 10, Exceptional, (13)
"Home was exactly as listed, very comfortable and convenient for my family’s trip. "
Relax or be active! The choice is yours in this pet-friendly family home.
Charming 1870 cape cottage in Litchfield
Outdoor pool

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (52)
"Great location and beautiful setting. Was perfect for the two of us."
Charming 1870 cape cottage in Litchfield
Woodland A-Frame
Interior

Woodland A-Frame

10.0 out of 10, Exceptional, (1)
"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "
Woodland A-Frame
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (5)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
County Seat Colonial
2 bedrooms, iron/ironing board, WiFi, bed sheets

County Seat Colonial

10.0 out of 10, Exceptional, (11)
"This was just what we needed. Thank you for a beautiful home, adorable town and so much to do! Perfect weekend for my family!"
County Seat Colonial
Charming Home with Fireplace and Indoor Pool in Sharon, CT
Terrace/patio

Charming Home with Fireplace and Indoor Pool in Sharon, CT

10.0 out of 10, Exceptional, (1)
"Our family had a wonderful stay at the beautiful, clean, peaceful Hoyt House. There was plenty of space to gather together as well as spread out. The daffodils were beginning to bloom and there is the sight and sound of a running stream behind the home. We were close to fun things to explore like the Audubon, covered bridge, and Kent waterfalls. Great bakery, restaurants, grocery a short drive away. The heated indoor swimming pool was the biggest hit. We hope to have the opportunity to...
Charming Home with Fireplace and Indoor Pool in Sharon, CT
Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
Fridge, microwave, oven, stovetop

Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB

Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
Renovated Lakefront House w/ Dock: Pets Welcome!
Terrace/patio

Renovated Lakefront House w/ Dock: Pets Welcome!

9.0 out of 10, Wonderful, (20)
"the lake house is terrific and having the boats and a fire pit was such a nice thing."
Renovated Lakefront House w/ Dock: Pets Welcome!
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (3)
"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."
The Race Mountain House
Beautiful retreat in a lake community to the enjoy the summer season.
Exterior

Beautiful retreat in a lake community to the enjoy the summer season.

10.0 out of 10, Exceptional, (40)
"The house was spacious and very comfortable for 6 people. The owner was very detailed and easy to reach! The area was very quiet and peaceful!"
Beautiful retreat in a lake community to the enjoy the summer season.
Spacious waterfront Berkshire home family private get-away
Property grounds

Spacious waterfront Berkshire home family private get-away

10.0 out of 10, Exceptional, (61)
"Had a nice extended weekend with friends, amazing waterfront views!"
Spacious waterfront Berkshire home family private get-away
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (47)
"What a wonderful property for our girls trip! The house is clean, there’s so much hangout space, and it’s so well supplied. "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Rustic 3bd Lake Front Country Cottage
Smart TV, fireplace, stereo

Rustic 3bd Lake Front Country Cottage

9.2 out of 10, Wonderful, (5)
"Enjoy our hikes and lake front view as well as kayaking around lake. Pretty area."
Rustic 3bd Lake Front Country Cottage
LAKE FRONT LAKE BUEL Monterey New Marlborough 10 M GREAT BARRINGTON PRIVATE DOCK
Fridge, microwave, oven, stovetop

LAKE FRONT LAKE BUEL Monterey New Marlborough 10 M GREAT BARRINGTON PRIVATE DOCK

10.0 out of 10, Exceptional, (41)
"We had a great time at the property. It has the best location on Lake Buel with an incredible view over the lake towards the sunset. The description was accurate."
LAKE FRONT LAKE BUEL Monterey New Marlborough 10 M GREAT BARRINGTON PRIVATE DOCK
Minutes from downtown Great Barrington, Convenient location
Exterior

Minutes from downtown Great Barrington, Convenient location

10.0 out of 10, Exceptional, (49)
"We had a great time, lots of space and a perfect home base for catamount, great Barrington, etc. "
Minutes from downtown Great Barrington, Convenient location
Lakeside Berkshire's Escape
Outdoor dining

Lakeside Berkshire's Escape

Lakeside Berkshire's Escape
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

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

10/10 Excellent
"The host was great and the property was wonderful. Extremely well kept house. The tennis court was such a unique touch to the home. It was such a peaceful home with lots of entertainment opportunities. The tree line made it feel so private. We really enjoyed having such easy access to Great Barrington and Stockbridge. Thank you"
John C. 4-night trip
Posted 2 days ago
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns