Main Street Historic District Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Main Street Historic District Vacation Homes

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (13)
"Very comfortable rockers and Adirondack chairs make it easy to relax and enjoy the lake view. Our bed was comfortable, and Nile supplied all we needed with linens and soaps. We appreciated all the space and large dining table. Lake is beautiful. Very enjoyable stay. Exceptional communication with our host. "
Grammy's Lake House w/ Private Waterfront Access

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

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 CA $401
CA $729 total
includes taxes & fees
Aug 11 - Aug 12
Modern Luxury, The Perfect Getaway Awaits

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (23)
"Right off the highway, very clean and kitchen was very well equipped. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

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 CA $183
CA $570 total
includes taxes & fees
Aug 14 - Aug 15
Private Apartment in Berlin

Modern & Cozy Cape | 4 Bedroom House | Central Location

10.0 out of 10, Exceptional, (5)
"We had a great stay in this house. It provided everything we needed for a comfortable and enjoyable visit. All the rooms were clean, tidy, and well-maintained, creating a welcoming environment. The host was exceptionally helpful and quick to respond to any questions or needs we had, which made our experience even better. We highly recommend this house for anyone looking for a hassle-free and pleasant stay."
The price is CA $179
CA $405 total
includes taxes & fees
Aug 10 - Aug 11
Modern & Cozy Cape | 4 Bedroom House | Central Location

Prime West Hartford Center: Timeless Charm

10.0 out of 10, Exceptional, (17)
"Very comfortable and clean accommodations in walking distance to stores and many restaurant options. Highly recommend for anyone needing lodging in West Hartford. "
Prime West Hartford Center: Timeless Charm

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

Private Yard & Covered Deck: Vintage Windsor Home

9.0 out of 10, Wonderful, (8)
"Great rentsl. The location was convenient to the airport. The house was clean and well kept. "
Private Yard & Covered Deck: Vintage Windsor Home

You and your Family deserve a break. Relax and enjoy lake front living

10.0 out of 10, Exceptional, (50)
"Every thing was great, nice property. Highly recommend."
You and your Family deserve a break. Relax and enjoy lake front living

Summer at the Haddam House

10.0 out of 10, Exceptional, (54)
"This is a lovely cottage on the river. Cannot wait to stay here again!"
Summer at the Haddam House

#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

Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

2.0 star property
9.2 out of 10, Wonderful, (9)
"Beautiful location, very comfortable for our small family."
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (17)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is CA $742
CA $1,225 total
includes taxes & fees
Aug 10 - Aug 11
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF

9.8 out of 10, Exceptional, (119)
"Very responsive owner in beautiful place! We enjoyed our time here."
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF

New!Quaint & Convenient Hideaway: Great Location

9.8 out of 10, Exceptional, (12)
"We had a wonderful stay. The property was clean and nicely decorated. The owner was very helpful and prompt with communication, even allowed us to check in a little early so we could settle in before seeing the new grandchild. "
New!Quaint & Convenient Hideaway: Great Location

Blue Back Bungalow

2.0 star property
9.4 out of 10, Exceptional, (14)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
The price is CA $181
CA $540 total
includes taxes & fees
Sep 8 - Sep 9
Blue Back Bungalow

Stylish, Relaxing & Comfy 3 BDR Home. 2 minutes to Lake Compounce

9.8 out of 10, Exceptional, (11)
"Communication with the host was easy and Davos is very nice with any questions we had. The interior of the house was clean, and we loved how it was decorated. We had a relaxing time and will definitely stay there again next time we visit Bristol. "
Stylish, Relaxing & Comfy 3 BDR Home. 2 minutes to Lake Compounce

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

10.0 out of 10, Exceptional, (1)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
The price is CA $207
CA $398 total
includes taxes & fees
Sep 8 - Sep 9
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Main Street Historic District Hotel Reviews