A coastal town with a lighthouse, houses, and a river.

Vacation Homes in Middlesex County

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Top Cities in Middlesex County

A steel bridge with a truss design spanning over a calm river, surrounded by lush greenery.
Vacation HomesVacation Homes

Cromwell

Cromwell
A white lighthouse with a red roof, surrounded by a well-maintained lawn and vibrant yellow flowers.
Vacation HomesVacation Homes

Clinton

Clinton

Our top choices for Middlesex County vacation homes

A porch with wicker furniture and a view of a road and greenery.

1. 4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy

4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
East Shore
10.0 out of 10, Exceptional, (50 reviews)
"Thank you place was enormous and beautiful"
United States
Kristin
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
A covered porch with a wooden table and wicker chairs, a vase with flowers, and a view of the street.

2. Stunning downtown Mystic 4 bedroom 2 kitchen newly renovated historic home

Stunning downtown Mystic 4 bedroom 2 kitchen newly renovated historic home
Mystic
10.0 out of 10, Exceptional, (2 reviews)
"Excellent. Meticulous. Well thought out for vacationers."
United States
Greg S.
Stunning downtown Mystic 4 bedroom 2 kitchen newly renovated historic home
A modern living room with a sofa, a dining table, and a TV mounted on the wall.

3. Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (75 reviews)
"All aspects of our stay were excellent!"
United States
Lori G.
The price is AED 327
AED 861 total
includes taxes & fees
16 Nov - 17 Nov
Cozy, comfy,quiet &close to casinos
A cozy dining area with a wooden table, cushioned chairs, and a view of the beach.

4. Waterfront Beach House

Waterfront Beach House
Clinton
9.6 out of 10, Exceptional, (73 reviews)
"We loved it and plan to visit again next year!!"
United States
Lynn M.
Waterfront Beach House
A modern living room with a fireplace, a large window with a view of a beach, and a 'Welcome to the Farm' sign.

5. Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT

Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT
Groton
10.0 out of 10, Exceptional, (146 reviews)
"Lovely property and super easy communication and check-in/check-out process with the host. Would definitely book again."
United States
Benjamin G.
The price is AED 1,410
AED 2,912 total
includes taxes & fees
15 Nov - 16 Nov
Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT
A room with a large window overlooking a swimming pool, wooden cabinets, and a view of a fenced backyard.

6. Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
East Lyme
10.0 out of 10, Exceptional, (124 reviews)
"The property at White Gate was absolutely stunning. It was perfect for our large group, with plenty of space and comfortable rooms for all. The pool was a huge added bonus and a ton of fun for everyone!"
United States
Mitchell R.
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
A porch with two white wicker chairs and a bench, surrounded by a wooden deck.

7. Gorgeous 3BR Beach House with Private Beach Access.

Gorgeous 3BR Beach House with Private Beach Access.
Pine Orchard
9.8 out of 10, Exceptional, (86 reviews)
"Hosts were very communicative and the house was perfect for a beach weekend!"
United States
Andrew K.
Gorgeous 3BR Beach House with Private Beach Access.
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

8. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (54 reviews)
"Great property and location. So easily walkable to everything. The host was super responsive, we had a great stay!"
United States
Carey D.
The price is AED 349
AED 890 total
includes taxes & fees
18 Nov - 19 Nov
Aqua Vista
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

9. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (15 reviews)
"Cute little house with excellent amenities. Perfect for our cousins getaway!"
United States
Karol T.
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A living room with a brown leather sofa, a wooden coffee table, and a lamp. There is a door with a window and a view of trees outside.

10. Coastal Victorian Home, Walk to Downtown

Coastal Victorian Home, Walk to Downtown
Mystic River Historic District
10.0 out of 10, Exceptional, (129 reviews)
"Great location, just steps away from everything in Mystic. Nice layout for a family get together."
United States
Mike J.
Coastal Victorian Home, Walk to Downtown
A sandy beach with a wooden fence in the foreground and a clear sky with clouds in the background.

11. Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
New London
8.0 out of 10, Very good, (31 reviews)
"Good location, great price, communication always great with the host. Accommodations were clean, decorative and comfortable. Heat and air, family friendly, and neat. Will return and recommend to friends and family!"
United States
Alicia W.
The price is AED 321
AED 808 total
includes taxes & fees
16 Nov - 17 Nov
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
A room with a large sliding glass door leading to a wooden deck with a white railing, overlooking a body of water.

12. Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
West Haven
10.0 out of 10, Exceptional, (63 reviews)
"A great place for our family get together!"
United States
Deborah S.
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Property grounds

13. The Bungalow at Eagleville Lake Under 3 miles to UCONN!

The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Coventry
10.0 out of 10, Exceptional, (97 reviews)
"Nice peaceful area for family trips. The nature around the lake is rich and beautiful."
United States
Eleonora N.
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
A spacious room with a large window overlooking a body of water, a round table, and a wicker chair.

14. The Lobster Shack Waterfront+ Dock - Casual Luxury of a New England Beach House

The Lobster Shack Waterfront+ Dock - Casual Luxury of a New England Beach House
Groton
10.0 out of 10, Exceptional, (2 reviews)
"Great place. House is very nice and view is amazing."
United States
John O.
The Lobster Shack Waterfront+ Dock - Casual Luxury of a New England Beach House
A modern kitchen with white cabinetry, stainless steel appliances, and a wooden island.

15. Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.

Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Stonington
10.0 out of 10, Exceptional, (78 reviews)
"Loved our stay, beautifully decorated inside and out. Conveniently located and so much within walking distance."
United States
Deborah J
The price is AED 1,157
AED 2,270 total
includes taxes & fees
15 Nov - 16 Nov
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
A modern house with a stone pathway leading to the entrance.

16. Luxurious midcentury modern glass house in the woods, chefs kitchen & great art

Luxurious midcentury modern glass house in the woods, chefs kitchen & great art
Old Lyme
10.0 out of 10, Exceptional, (30 reviews)
"Beautiful home and landscaping. Well equipped kitchen and spice drawers. The house is full of delightful art work, very peaceful environment."
United States
Susan C.
Luxurious midcentury modern glass house in the woods, chefs kitchen & great art
A stone pier leading to a beach with houses in the background.

17. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (69 reviews)
"We absolutely loved this cottage.. It was very clean. It had everything we needed. We loved the area so much,, the surrounding residents were so friendly to us.. We would love to book again next year.Thank you for sharing your home.."
United States
Joanne M.
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A wooden pathway leading to a beach with scattered rocks and greenery.

18. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is AED 716
AED 1,574 total
includes taxes & fees
15 Nov - 16 Nov
Beach Block Hideaway
A covered outdoor seating area with a white sofa, chairs, and a table with a decorative item.

19. Autumn in East Hampton! Private Beach Community, Hot Tub, Pirate Ship and More!

Autumn in East Hampton! Private Beach Community, Hot Tub, Pirate Ship and More!
East Hampton
9.8 out of 10, Exceptional, (94 reviews)
"Amazing property for kids. Exceeded expectations. Host was very communicative."
United States
Carter P.
Autumn in East Hampton! Private Beach Community, Hot Tub, Pirate Ship and More!
A beach with waves gently lapping onto the shore, a clear sky, and the sun setting in the distance.

20. Cozy Cottage - Beach - Lighthouse Views - Dedicated Office

Cozy Cottage - Beach - Lighthouse Views - Dedicated Office
New London
10.0 out of 10, Exceptional, (27 reviews)
"Fabulous stay. Great location. Excellent support!"
United States
Brandon B.
Cozy Cottage - Beach - Lighthouse Views - Dedicated Office
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 Middlesex County Hotel Reviews

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Good location to Yale university."
Stephanie 1-night trip
Posted 1 hour ago
New Haven Hotel

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