Holiday Homes in Cheshire Historic District

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Featured Holiday Homes in Cheshire Historic District and around

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (30)
"A very comfortable short stay in a convenient location"
Cozy 2 bedroom home located minutes from downtown

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (14)
"My family and I stayed at the property for a wedding in Milford. The house had plenty of space for our group to say, and the bedrooms were comfortable. The three bathrooms were helpful for our group to efficiently get ready for the wedding, and the kitchen was adequately appointed for us to have meals."
The price is €447
includes taxes & fees
28 Sept - 29 Sept
McAngel Haven: 5 mins from Yale

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

9.4 out of 10, Exceptional, (14)
"This Carriage House is exactly as described. Wonderful location and setting, just steps away from Branford Point. Hope to visit again soon! "
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (14)
"Solid location and quiet neighborhood good after a long day."
Ranch style living at its best with country garden & patio!

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (68)
"Great family get together where we all were very comfortable. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

10.0 out of 10, Exceptional, (5)
The price is €248
includes taxes & fees
28 Sept - 29 Sept
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

Amazing Lakefront Property

9.8 out of 10, Exceptional, (26)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property

Clear LI Sound waterview, Wedding pics, Yale&Beach

10.0 out of 10, Exceptional, (7)
"Attended a wedding close by. This house was a comfortable clean place to rest in between events. Lovely water front. Calm and peaceful"
The price is €530
includes taxes & fees
28 Sept - 29 Sept
Clear LI Sound waterview, Wedding pics, Yale&Beach

3-bedroom house just walking distance from Yale and Downtown

The price is €358
includes taxes & fees
29 Sept - 30 Sept
3-bedroom house just walking distance from Yale and Downtown

Cozy East Haven Home • Near Beach & Yale

10.0 out of 10, Exceptional, (3)
"Beautiful seaside cottage. Updated and well appointed, bidet, fire pit and more. Very close to several beaches. Driving distance to many attractions, statue of liberty, and more. I would stay again. "
The price is €131
includes taxes & fees
30 Sept - 1 Oct
Cozy East Haven Home • Near Beach & Yale

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (13)
"The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!"
Family Stays: Middletown, CT

The Connecticut Chalet - On 5 Acres!

9.8 out of 10, Exceptional, (7)
"Highly recommend this property if you're heading to the area!"
The Connecticut Chalet - On 5 Acres!

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 €304
includes taxes & fees
22 Oct - 23 Oct
Private Apartment in Berlin

Cozy newly remodeled home close to major amenities in Connecticut a

8.4 out of 10, Very good, (18)
"I stayed for about two days and nights and had a great experience. The house was clean, everything we needed was easy to find, the only thing was that the shower was a little clogged. Overall, it was a great experience!!"
Cozy newly remodeled home close to major amenities in Connecticut a

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

10.0 out of 10, Exceptional, (3)
" 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

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 €384
includes taxes & fees
13 Oct - 14 Oct
Westshore Luxury

Family Gem on Dyer Street

10.0 out of 10, Exceptional, (1)
"The check in process was simple and easy. The house was exactly as pictured and perfect for 7 guests. It was clean and had all the amenities."
The price is €832
includes taxes & fees
28 Sept - 29 Sept
Family Gem on Dyer Street

Modern Beach Home - Waterview, close to restaurants, universities and hospitals

10.0 out of 10, Exceptional, (3)
"Great stay at this lovely house. Walk to beach! Perfect backyard to enjoy a beautiful weekend "
Modern Beach Home - Waterview, close to restaurants, universities and hospitals

Direct Waterfront Private Beach Escape

9.6 out of 10, Exceptional, (19)
"Thank you so Much, the family had a great time. Found some good seaglass"
Direct Waterfront Private Beach Escape

Relax by the River | Branford Waterfront Home

8.4 out of 10, Very good, (5)
"Clean, family friendly, and fun."
Relax by the River | Branford Waterfront 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

Find out more about Cheshire Historic District

Find out more about Cheshire Historic District

Cheshire Historic District Holiday Homes information

Number of reviews
222
Accommodation
243 Holiday Homes
Lowest Price
€131
Highest Price
€832