Holiday Homes in Cheshire Historic District

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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 Cheshire Historic District and around

Cozy 2 bedroom home located minutes from downtown
Kitchen features a central island, microwave, coffee maker, and dining table with four chairs.

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (29)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown
Cozy 3 bedroom minutes from Yale and the beach
Kitchen features a central island, oven, and white cabinetry with a patterned backsplash.

Cozy 3 bedroom minutes from Yale and the beach

7.4 out of 10, Good, (3)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach
Tranquil Litchfield Connecticut Retreat".
Relax by the fire pit in a serene outdoor seating area surrounded by Adirondack chairs.

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (15)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is €280
includes taxes & fees
10 Aug - 11 Aug
Tranquil Litchfield Connecticut Retreat".
New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan
Enjoy cooking in this well-lit kitchen with a refrigerator, microwave, and double oven.

New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan

2.0 star property
10.0 out of 10, Exceptional, (6)
"Everything about our stay at this property was great. Communication, check-in, cleanliness, etc. The location is directly across the street from Wesleyan University which made my son's visit all the better. I will definately stay here again."
New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Enjoy a refreshing dip in the pool surrounded by a deck and basketball hoop.

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (136)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Gorgeous 4BR Beach House with Private Beach Access.
Guests can enjoy beach access with a sandy shoreline and ocean views.

Gorgeous 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (74)
"We loved our stay at this beautiful cottage. The entire experience was very smooth, from pre-check in to getting there and even offers to help with anything we needed in our stayThe cottage is very cozy and well-cared for. The rooms are comfortable and the Internet fast. There is a lot to do in the area, with New Haven nearby and many good restaurants."
Gorgeous 4BR Beach House with Private Beach Access.
Modern Luxury, The Perfect Getaway Awaits
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a dining area.

Modern Luxury, The Perfect Getaway Awaits

10.0 out of 10, Exceptional, (2)
"Super clear, spacious, house looks just like the photos. Very easy communication with the host. Thank you!"
The price is €602
includes taxes & fees
20 Aug - 21 Aug
Modern Luxury, The Perfect Getaway Awaits
Cozy Lakefront Bungalow w firepit/dock/kayaks
Enjoy the view from the upper balcony, which offers a fire pit and Adirondack chairs in the yard.

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
Beach Bungalow, walk to beach, private backyard
Fridge, microwave, oven, dishwasher

Beach Bungalow, walk to beach, private backyard

10.0 out of 10, Exceptional, (3)
"The property was perfect for all of us. It was in a quiet neighborhood and great location."
Beach Bungalow, walk to beach, private backyard
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Enjoy a well-equipped kitchen with a central sink, stainless steel faucet, and a window offering a view of the surrounding greenery.

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (27)
"Clean, Cozy and Comfortable "
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Private Apartment in Berlin
Fridge, microwave, oven, stovetop

Private Apartment in Berlin

2.0 star property
9.2 out of 10, Wonderful, (5)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
The price is €363
includes taxes & fees
14 Aug - 15 Aug
Private Apartment in Berlin
Family Gem on Dyer Street
Dining

Family Gem on Dyer Street

The price is €797
includes taxes & fees
11 Aug - 12 Aug
Family Gem on Dyer Street
The Jewel of The Cove - Historic Coastal Retreat
Enjoy a serene beach experience with sailboats on the calm sea and palm trees along the shoreline.

The Jewel of The Cove - Historic Coastal Retreat

2.0 star property
10.0 out of 10, Exceptional, (4)
"loved it so much, beautiful property 100 % would stay again "
The price is €449
includes taxes & fees
17 Aug - 18 Aug
The Jewel of The Cove - Historic Coastal Retreat
McAngel Haven: 5 mins from Yale
Kitchen features a stainless steel range hood, dishwasher, and microwave.

McAngel Haven: 5 mins from Yale

10.0 out of 10, Exceptional, (12)
"Had a wonderful but short stay in New Haven. Home.of PEZ and PIZZA . "
The price is €459
includes taxes & fees
10 Aug - 11 Aug
McAngel Haven: 5 mins from Yale
Spacious 4-bedroom house with AC, WiFi in welcoming Guilford
Relax in a spacious living area with a comfortable sofa and dining space for casual meals or entertaining.

Spacious 4-bedroom house with AC, WiFi in welcoming Guilford

10.0 out of 10, Exceptional, (2)
" The house was awesome, had an very good layout, great yard, nice deck and it was the perfect place for our group! Great communication with the owner!"
Spacious 4-bedroom house with AC, WiFi in welcoming Guilford
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather
Enjoy cooking in this well-equipped kitchen with a gas stove, oven, and ample countertop space.

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

10.0 out of 10, Exceptional, (12)
"The house was as advertised and located in a really quiet neighborhood. The host was easy to work with and responded to me each time I texted her. If the opportunity ever comes up again, we would definitely stay at this property again."
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
Enjoy a formal outdoor dining experience surrounded by lush greenery and tall trees.

Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

2.0 star property
10.0 out of 10, Exceptional, (8)
"We met our kids (who live on the east coast) at Natures Nest and really enjoyed our time here. We cooked 2 big meals and the kitchen had everything we needed…even spices & coffee. And Marco left some apples, sweets and wine for us! He was very responsive and helpful anytime we had questions, and gave us great recommendations. Everything was great!"
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
3 bedroom home( 2 Kings and 1 queen), 4 Mins From Beach!
Enjoy cooking in this kitchen with a refrigerator, dishwasher, and ample natural light.

3 bedroom home( 2 Kings and 1 queen), 4 Mins From Beach!

9.4 out of 10, Exceptional, (12)
"The owners clearly want you to enjoy your stay and work hard at covering all the bases."
3 bedroom home( 2 Kings and 1 queen), 4 Mins From Beach!
Westshore Luxury
Relax in the patio area with comfortable seating and a small dining table.

Westshore Luxury

7.0 out of 10, Good, (4)
"Perfect location near the beach! When we stayed the weather wasn’t ideal for the beach day but I can only imagine how perfect this house would be in a beautiful day! The host had a wagon and beach toys available as well which was wonderful. Very cute property. I was unsure of our check out instructions other than to ensure we cleaned our dishes and messaged the host and never heard back but other than that our stay was great. "
The price is €391
includes taxes & fees
31 Aug - 1 Sept
Westshore Luxury
#26 Beautifully Renovated 2 BR Home
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, dishwasher, and coffee maker.

#26 Beautifully Renovated 2 BR Home

10.0 out of 10, Exceptional, (2)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
#26 Beautifully Renovated 2 BR Home
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 Cheshire Historic District Hotel Reviews

Woodspring Suites Newington - Hartford South

Woodspring Suites Newington - Hartford South

10/10 Excellent
"amazing suite to.enjoy ams sf as y confartably "
CHRISTINE 1-night trip
Posted 2 days ago
Woodspring Suites Newington - Hartford South