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

Vacation Rentals in Middlesex County

Top Cities in Middlesex County

A forested landscape with a winding dirt road and power lines.
Vacation RentalsVacation Rentals

Middletown

Middletown

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, (183 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."
United States
Frank
$207 nightly
The price is $238
Sep 2 - Sep 3
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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.

2. 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, (36 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.
$228 nightly
The price is $258
Sep 7 - Sep 8
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A large, white, multi-story building with a prominent tower and a flag on top.

3. 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.
$216 nightly
The price is $245
Sep 1 - Sep 2
Total with taxes and fees
Walk To Goodspeed Opera House!
A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

4. 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.
$295 nightly
The price is $333
Aug 30 - Aug 31
Total with taxes and fees
2BR Apartment Near Wesleyan 301
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

5. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (53 reviews)
"We enjoyed our stay"
United States
JM B.
$210 nightly
The price is $238
Aug 30 - Aug 31
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
A lakeside property with a gazebo, dock, kayaks, and a flag.

6. 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.
$292 nightly
The price is $330
Sep 7 - Sep 8
Total with taxes and fees
Lakeview Carriage House with Spectacular Sunset Views
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

7. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$291 nightly
The price is $329
Sep 1 - Sep 2
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

8. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (5 reviews)
$251 nightly
The price is $284
Aug 31 - Sep 1
Total with taxes and fees
2BR Apartment Near Wesleyan 102
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

9. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"It was close to a very pretty beach, which was nice. The neighborhood is very quiet. The only downside was that the bedrooms were up stairs and the stairs were very steep. I didn’t notice that in the write up to the property it might have changed my rental of it. I would rate it very highly for anyone that doesn’t have trouble with stairs. The air conditioning was excellent, and the property is well appointed the owners were lovely and responsive."
United States
Sandra Hart
$399 nightly
The price is $451
Sep 9 - Sep 10
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

10. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Clean apartment plenty of parking"
United States
Rebecca P.
$339 nightly
The price is $383
Sep 22 - Sep 23
Total with taxes and fees
3 BR Apartment Near Wesleyan 201
A beach with waves, a clear sky, and a sandy shore.

11. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
$325 nightly
The price is $367
Sep 1 - Sep 2
Total with taxes and fees
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A modern kitchen with white cabinets, a stainless steel refrigerator, a dining area with two chairs, and a coffee machine.

12. “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.
$256 nightly
The price is $290
Aug 31 - Sep 1
Total with taxes and fees
“3BR Home Near Wesleyan & Downtown Middletown
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

13. 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.
$537 nightly
The price is $608
Sep 21 - Sep 22
Total with taxes and fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

14. 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.
$630 nightly
The price is $713
Sep 22 - Sep 23
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
A glass-enclosed patio with a wooden table and wicker chairs, surrounded by glass doors and windows offering views of a wooded area.

15. LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"Was very happy with how wonderfully beautiful the place was. The host was excellent and answered any questions I had promptly. I really appreciate how nice he was."
United States
Elizabeth C.
$669 nightly
The price is $757
Sep 28 - Sep 29
Total with taxes and fees
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
A two-story house with a front porch, a garage, and a well-maintained lawn.

16. 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.
$759 nightly
The price is $858
Sep 28 - Sep 29
Total with taxes and fees
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
An aerial view of a marina with boats docked, surrounded by residential buildings and greenery.

17. 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.
$672 nightly
The price is $760
Sep 24 - Sep 25
Total with taxes and fees
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

18. 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.
$705 nightly
The price is $797
Aug 31 - Sep 1
Total with taxes and fees
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
A modern kitchen with a central island, bar stools, and pendant lighting.

19. 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)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
$909 nightly
The price is $1,029
Aug 29 - Aug 30
Total with taxes and fees
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A spacious room with a large dining table and chairs, a sofa, and large windows offering a view of the sea and buildings.

20. 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.
$830 nightly
The price is $943
Sep 24 - Sep 25
Total with taxes and fees
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
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
"We had a pleasant experience with New Haven Hotel. Check-in and check-out were very smooth and fast. The hotel staff, especially the front desk staff, were very friendly, warm, and helpful. The hotel's location was great, right in New Haven Business district and walkable to Yale University campus. We would highly recommend this hotel if you are planning to visit Yale or New Haven."
James 1-night trip
Posted 5 hours ago
New Haven Hotel

Find out more about Middlesex County

Discover your perfect Middlesex County vacation rental with Expedia

How many vacation rentals are available in Middlesex County?


Expedia has plenty of vacation rentals to choose from in and around  Middlesex County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Middlesex County?


The selection of Middlesex County vacation rentals we have selected for you start as low as $238 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Middlesex County?


Vacation rentals in Middlesex County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Middlesex County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Middlesex County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Middlesex County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Middlesex County?


Find vacation rentals in Middlesex County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Middlesex County.  


What amenities are available in a vacation rental in Middlesex County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Middlesex County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Middlesex County?   


Everytime is a great time to head to Middlesex County! Staying in a Middlesex County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


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Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Middlesex County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.