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

Vacation Rentals in Middlesex County

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Our top choices for Middlesex County vacation rentals

A cabin with a large window, surrounded by trees.

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (181 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."
United States
Frank
The price is ￥21,458
￥39,300 total
includes taxes & fees
Sep 21 - Sep 22
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A large, white, multi-story building with a prominent tower and a flag on top.

2. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (40 reviews)
"Simple process, plenty of room, ample parking and no issues with noise from the business above. "
United States
Amber J.
The price is ￥28,929
￥47,653 total
includes taxes & fees
Sep 1 - Sep 2
Walk To Goodspeed Opera House!
A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

3. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (3 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
The price is ￥26,545
￥58,979 total
includes taxes & fees
Aug 25 - Aug 26
2BR Apartment Near Wesleyan 301
A modern kitchen with a central island, bar stools, and pendant lighting.

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

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is ￥103,318
￥164,355 total
includes taxes & fees
Aug 28 - Aug 29
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

5. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (35 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is ￥19,869
￥41,009 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

6. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (1 review)
"Clean apartment plenty of parking"
United States
Rebecca P.
The price is ￥29,247
￥62,563 total
includes taxes & fees
Sep 3 - Sep 4
3 BR Apartment Near Wesleyan 201
A two-story house with a front porch, a garage, and a well-maintained lawn.

7. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Middletown
9.8 out of 10, Exceptional, (17 reviews)
"Large, comfortable house in a tranquil part of town. "
United States
Daryl R.
The price is ￥77,822
￥135,313 total
includes taxes & fees
Sep 21 - Sep 22
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A stone fire pit with two Adirondack chairs, a wooden fence, and a black building with a red door.

8. NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (8 reviews)
"We really enjoyed our stay here. The house has a cozy, homey feel and was a nice place to come back to after being out for the day. It was quiet, comfortable, and had a relaxed vibe that made the trip easy.The location was a big plus for us. Hammonasset Beach was only a few minutes away, and Madison center was just as close, which made it easy to grab dinner or pop out for anything we needed. The outdoor fireplace was also a really nice touch and made the evenings feel special.Overall, it was a...
United States
Moe B.
The price is ￥46,893
￥60,603 total
includes taxes & fees
Aug 23 - Aug 24
NEW Coastal Cottage 2 Miles to Beach + Lake Access
A lakeside property with a gazebo, dock, kayaks, and a flag.

9. Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is ￥24,639
￥52,179 total
includes taxes & fees
Sep 7 - Sep 8
Lakeview Carriage House with Spectacular Sunset Views
A modern office space with a sofa, two round tables, and a coffee table. There are chairs around the tables, a rug on the floor, and a door in the background.

10. Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is ￥114,444
￥146,552 total
includes taxes & fees
Aug 28 - Aug 29
Conference Room Rental no sleeping arrangements
A modern kitchen with white cabinets, a stainless steel refrigerator, a dining area with two chairs, and a coffee machine.

11. “3BR Home Near Wesleyan & Downtown Middletown

“3BR Home Near Wesleyan & Downtown Middletown
Washington Street Historic District
7.8 out of 10, Good, (6 reviews)
"Nice place"
United States
Jousette C.
“3BR Home Near Wesleyan & Downtown Middletown
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

12. Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Westbrook Center
9.4 out of 10, Exceptional, (3 reviews)
"We had a lovely time during our stay. The hosts were excellent with communication and quick responses throughout our stay. The 2 family suites were perfect for our families to all stay together during this trip. We would definitely book again! "
United States
Kate G.
The price is ￥76,046
￥133,114 total
includes taxes & fees
Aug 23 - Aug 24
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
A spacious room with a large dining table and chairs, a sofa, and large windows offering a view of the sea and buildings.

13. Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Old Saybrook
9.8 out of 10, Exceptional, (41 reviews)
"Enjoyed our stay"
United States
Nicole L.
The price is ￥190,752
￥287,559 total
includes taxes & fees
Sep 6 - Sep 7
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
A beach with waves, a clear sky, and a sandy shore.

14. 1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Great spot Very clean"
United States
Dorothy W.
The price is ￥37,696
￥82,559 total
includes taxes & fees
Sep 15 - Sep 16
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
An aerial view of a marina with boats docked, surrounded by residential buildings and greenery.

15. Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (51 reviews)
"Great spot easy walk to the water and very close to town!"
United States
Genevieve G.
The price is ￥81,833
￥135,358 total
includes taxes & fees
Aug 24 - Aug 25
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

16. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is ￥50,864
￥96,085 total
includes taxes & fees
Sep 21 - Sep 22
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

17. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ￥17,883
￥35,326 total
includes taxes & fees
Sep 15 - Sep 16
1-bedroom cottage with Grove Beach 🏖️ access.
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

18. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (5 reviews)
The price is ￥15,880
￥40,628 total
includes taxes & fees
Aug 23 - Aug 24
2BR Apartment Near Wesleyan 102
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

19. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥50,006
￥116,994 total
includes taxes & fees
Sep 15 - Sep 16
Beachside Bliss w/ Game Room, Gym & Golf Green
A dining room with a rectangular table and four chairs, a window with blinds, a recessed ceiling light, and a wall-mounted air conditioning unit.

20. 3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202
Washington Street Historic District
8.0 out of 10, Very Good, (1 review)
"The apartment is the first floor of a two story duplex. It was very clean and larger than we were expecting. We had just about everything we needed for our stay. We really appreciate being able to bring our pets with us. I enjoyed walking around the neighborhood with my dog."
United States
Douglas M.
The price is ￥34,971
￥76,062 total
includes taxes & fees
Aug 25 - Aug 26
3 BR Apartment Near Wesleyan 202
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

The Capitol Hotel

The Capitol Hotel

8/10 Good
"Great location near the train and bus station; 2 minute walk and close to downtown for happy hour. While the decor is dated; the room was big with drawers, a closet with hangers and not hipster. It isn't a vacay hotel but it is certainly a location place. Breakfast was as good as most 3 star hotels."
Harvey 1-night trip
Posted 1 hour ago
The Capitol Hotel

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Vacation Apartments in Middlesex County

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