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Middle Haddam Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Middle Haddam vacation rentals

View from property

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, (186 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
$219 nightly
The price is $252
Oct 5 - Oct 6
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Living area

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.
$233 nightly
The price is $264
Sep 22 - Sep 23
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Property grounds

3. 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.
Lakeview Carriage House with Spectacular Sunset Views
Property grounds

4. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
$381 nightly
The price is $413
Sep 20 - Sep 21
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat
Exterior

5. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (42 reviews)
"Simple process, plenty of room, ample parking and no issues with noise from the business above. "
United States
Amber J.
$256 nightly
The price is $290
Sep 9 - Sep 10
Total with taxes and fees
Walk To Goodspeed Opera House!
Dining

6. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (5 reviews)
$249 nightly
The price is $281
Sep 7 - Sep 8
Total with taxes and fees
2BR Apartment Near Wesleyan 102
Exterior

7. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (30 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
$220 nightly
The price is $249
Sep 30 - Oct 1
Total with taxes and fees
Family Stays: Middletown, CT
Dining

8. 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.
$304 nightly
The price is $344
Sep 9 - Sep 10
Total with taxes and fees
3 BR Apartment Near Wesleyan 201
Interior

9. 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
Sep 5 - Sep 6
Total with taxes and fees
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Interior

10. Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
$442 nightly
The price is $499
Sep 7 - Sep 8
Total with taxes and fees
Cozy basement apartment with private bathroom, kitchen and entrance.
Interior

11. Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
$823 nightly
The price is $931
Sep 5 - Sep 6
Total with taxes and fees
Conference Room Rental no sleeping arrangements
Apartment, City View | Living area

12. Trumbull Apartments

Trumbull Apartments
3.0 star property
Downtown Hartford
2.0 out of 10, (1 review)
"Terrible, worst stay ever . It was such a hassle to get in no clear instructions… never again"
United States
Nicolas
$268 nightly
The price is $308
Sep 6 - Sep 7
Total with taxes and fees
Trumbull Apartments
Room

13. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$274 nightly
The price is $292
Sep 6 - Sep 7
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Living area

14. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
$274 nightly
The price is $292
Sep 20 - Sep 21
Total with taxes and fees
Newly Remodeled 1-BR Close to Everything yet Very Private
Exterior

15. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
$274 nightly
The price is $292
Sep 7 - Sep 8
Total with taxes and fees
All New 1BR with tons of Charm
Dining

16. 1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
10.0 out of 10, Exceptional, (1 review)
"This property is absolutely beautiful and well maintained. We stayed for three weeks with no problems or issues. Everything was clean and the kitchen has plenty of dishes, silverware, pots and pans. The dishwasher was a bonus making clean up easy and the grill was great allowing us to grill many meals. The owner was not only quick to respond but very helpful. Pet friendly was great for us so our medium size dog could travel with us. Excellent location in central CT with many stores and...
United States
Diane W.
$310 nightly
The price is $337
Sep 20 - Sep 21
Total with taxes and fees
1 Min to I-91 - Newly Renovated Modern 2 BR Home
Dining

17. 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.
$365 nightly
The price is $413
Sep 9 - Sep 10
Total with taxes and fees
3 BR Apartment Near Wesleyan 202
Living area

18. Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
$274 nightly
The price is $292
Sep 10 - Sep 11
Total with taxes and fees
Newly Remodeled with deck. Close to town center
Beach

19. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.0 out of 10, Wonderful, (48 reviews)
"The property was clean and accommodating."
United States
Ann Marie T.
$233 nightly
The price is $264
Sep 10 - Sep 11
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Private kitchen

20. 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)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
$291 nightly
The price is $329
Sep 8 - Sep 9
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
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 Middle Haddam Hotel Reviews

Holiday Inn Express Hartford South - Rocky Hill by IHG

Holiday Inn Express Hartford South - Rocky Hill by IHG

8/10 Good
"Our stay went very well"
Joey 1-night trip
Posted 1 hour ago
Holiday Inn Express Hartford South - Rocky Hill by IHG

Find out more about Middle Haddam

Everything you need to know about Middle Haddam vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middle Haddam vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middle Haddam vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middle Haddam vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middle Haddam. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middle Haddam in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $237 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middle Haddam rentals

At Expedia, we put the best Middle Haddam vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middle Haddam rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middle Haddam vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middle Haddam. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Middle Haddam?

Yes, we have vacation rentals near the most popular local attractions in Middle Haddam, or you can go with a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Middle Haddam has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: Visitors like this Middle Haddam vacation home rental. It is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Middle Haddam?

While exploring the area, visit family-friendly sights like Brownstone Exploration & Discovery Park, or get outside and enjoy nature at Connecticut River. In the larger area, you’ll find Hurd State Park and Machimoodus State Park.

What are vacation rentals like in Middle Haddam?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Middle Haddam. Vacation rentals offer amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a small group gathering.