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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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
Two wooden benches facing a calm body of water under a clear sky.
Vacation HomesVacation Homes

Clinton

Clinton

Our top choices for Middlesex County vacation homes

Exterior

1. The Hampton Sack a cheerful relaxing beach cottage

The Hampton Sack a cheerful relaxing beach cottage
East Hampton
6.6 out of 10, (24 reviews)
"Had a great time, will be back!"
United States
Patrick D.
The Hampton Sack a cheerful relaxing beach cottage
Dining

2. Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
Fair Haven
6.8 out of 10, (3 reviews)
"Blankets where itchy and smelled dirty small room when whole house was listed"
United States
Isabella R.
The price is AED 374
AED 504 total
includes taxes & fees
9 Sep - 10 Sep
Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
Terrace/patio

3. Phenomenal One Bedroom Cottage in Historic Old Lyme, Connecticut

Phenomenal One Bedroom Cottage in Historic Old Lyme, Connecticut
Old Lyme
10.0 out of 10, Exceptional, (2 reviews)
"Very quiet, comfortable, clean, the lanai was a nice touch, and the landscaping was nicely done too."
United States
David T.
Phenomenal One Bedroom Cottage in Historic Old Lyme, Connecticut
Outdoor dining

4. Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
Southold
10.0 out of 10, Exceptional, (41 reviews)
"Amazing location and great house! We loved it!"
United States
claire b.
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
Beach nearby, beach towels

5. Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly

Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
Saybrook Manor
9.8 out of 10, Exceptional, (55 reviews)
"Great stay with our daughter and dogs. Backyard and walls around the neighborhood and to downtown were great! Thank you!"
United States
Patricia P.
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
Exterior

6. Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (62 reviews)
"It was great ocation for a weekend get away with friends to Mohegan Sun"
United States
Teresa M.
The price is AED 591
AED 1,242 total
includes taxes & fees
8 Sep - 9 Sep
Cozy, comfy,quiet &close to casinos
Private kitchen

7. 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, (68 reviews)
"Can’t wait to come back!"
United States
Jackie M.
The price is AED 1,322
AED 2,589 total
includes taxes & fees
11 Aug - 12 Aug
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Beach

8. Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!
Westbrook Center
10.0 out of 10, Exceptional, (12 reviews)
"We had a great stay at the beach house! Luanne was a super-responsive host and communication with her throughout the stay through the app was a breeze. "
United States
Virgil C.
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!
Marina

9. Walk to Historic Downtown Mystic! <br>Best Location—beach, marinas, eateries!

Walk to Historic Downtown Mystic! <br>Best Location—beach, marinas, eateries!
West Mystic
9.4 out of 10, Exceptional, (30 reviews)
"Awesome place to stay in Mystic! Our hostess welcoming and provided us with everything we needed! "
United States
Grace K.
Walk to Historic Downtown Mystic! <br>Best Location—beach, marinas, eateries!
Property grounds

10. Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Mystic River Historic District
9.8 out of 10, Exceptional, (174 reviews)
"Great location "
United States
Brian S.
The price is AED 683
AED 1,354 total
includes taxes & fees
11 Aug - 12 Aug
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Beach nearby, sun loungers, beach towels

11. Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking

Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking
Niantic
10.0 out of 10, Exceptional, (49 reviews)
"Great property and location. Will stay again. "
United States
Kyle K.
Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking
Sun loungers, beach towels

12. Aqua Vista

Aqua Vista
Pipes Cove
9.8 out of 10, Exceptional, (40 reviews)
"Nice clean space, well appointed and easy walking access to downtown area."
United States
Molly G.
The price is AED 716
AED 1,410 total
includes taxes & fees
1 Sep - 2 Sep
Aqua Vista
Marina

13. LUX, Fireplace, Deck, Foosball, Pingpong, Private, Firepit, Multi-Gen Layout

LUX, Fireplace, Deck, Foosball, Pingpong, Private, Firepit, Multi-Gen Layout
West Mystic
10.0 out of 10, Exceptional, (36 reviews)
"Sparkling clean, well stocked, exactly as advertised property. The owner is responsive and easy to communicate with. Beautiful property! "
United States
Shirley M.
The price is AED 2,084
AED 4,236 total
includes taxes & fees
11 Aug - 12 Aug
LUX, Fireplace, Deck, Foosball, Pingpong, Private, Firepit, Multi-Gen Layout
Living area

14. Coastal Vibes 3BR in Mystic w/ Private Backyard, Outdoor Shower & Firepit

Coastal Vibes 3BR in Mystic w/ Private Backyard, Outdoor Shower & Firepit
Stonington
10.0 out of 10, Exceptional, (8 reviews)
"We had a wonderful stay at the house which was a perfect location with easy access to everything in town. "
United States
Norm O.
Coastal Vibes 3BR in Mystic w/ Private Backyard, Outdoor Shower & Firepit
Exterior detail

15. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (3 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
Bear Retreat - 2-bedroom house in Waterbury
Coffee/tea maker, microwave, oven, stovetop

16. Charming Mattituck Retreat Near the Bay with Modern Updates

Charming Mattituck Retreat Near the Bay with Modern Updates
Mattituck
10.0 out of 10, Exceptional, (1 review)
"Perfect place for family of 6! Everything was so clean. Beds were comfortable and it was close to tons of things to do in the area. Wed definitely stay again."
United States
Fred R.
Charming Mattituck Retreat Near the Bay with Modern Updates
Interior

17. Waterfront 3-bedroom w Firepit, Game Room, ~1 mile to Foxwoods, Great Wolf Lodge

Waterfront 3-bedroom w Firepit, Game Room, ~1 mile to Foxwoods, Great Wolf Lodge
Preston
9.0 out of 10, Wonderful, (31 reviews)
"Nice space, perfect location for our home base our vacation! Only wish the weather was nicer and we could’ve spent some time on the lake as well :)"
United States
Tabitha
Waterfront 3-bedroom w Firepit, Game Room, ~1 mile to Foxwoods, Great Wolf Lodge
Beach nearby

18. 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, (25 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 360
AED 889 total
includes taxes & fees
9 Sep - 10 Sep
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Terrace/patio

19. New Madison beach house - Ocean front- Great views- booking Summer 2026

New Madison beach house - Ocean front- Great views- booking Summer 2026
Madison
10.0 out of 10, Exceptional, (75 reviews)
"Always a great vacation."
United States
Matthew H.
New Madison beach house - Ocean front- Great views- booking Summer 2026
Outdoor pool

20. 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, (118 reviews)
"The host is very welcoming and the house is very comfortable and spacious"
United States
Douglas L.
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
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

Spark by Hilton Mystic Groton

Spark by Hilton Mystic Groton

10/10 Excellent
"Room was very clean and staff was very attentive, checking in to make sure we had what we needed and quickly bringing us things we requested (I.e. more towels). Breakfast was a bit lacking in options but not bad. Pool was great, lots of seats and clean. Perfect for my kids to enjoy in the afternoon. Would definitely stay here again."
Michael 2-night trip
Posted 2 hours ago
Spark by Hilton Mystic Groton

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