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Middle Haddam Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Middle Haddam vacation rentals

A cabin with a dining table set for two, a bicycle, and a small porch area.

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, (192 reviews)
"ABSOLUTELY BEAUTIFUL AND SERENE STAY . WE REALLY ENJOYED OUR STAY !"
United States
Melissa
$167 nightly
The price is $192
Oct 1 - Oct 2
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, (37 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
$222 nightly
The price is $252
Oct 19 - Oct 20
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A modern living room with a sofa, a dining table, and a massage chair.

3. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.0 out of 10, Wonderful, (7 reviews)
"Great place! "
United States
Gail R.
$446 nightly
The price is $479
Oct 7 - Oct 8
Total with taxes and fees
#29 - Modern 5 Bedroom/2 Bath
A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

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.
$299 nightly
The price is $322
Sep 28 - Sep 29
Total with taxes and fees
#24 Serenity A Lakefront Cottage Retreat
A modern kitchen with a central island, bar stools, and pendant lighting.

5. 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
10.0 out of 10, Exceptional, (32 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.
$856 nightly
The price is $976
Sep 27 - Sep 28
Total with taxes and fees
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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.

6. 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.
$383 nightly
The price is $437
Oct 1 - Oct 2
Total with taxes and fees
3 BR Apartment Near Wesleyan 202
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

7. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (6 reviews)
"Excellent beds and clean."
United States
DANIEL M.
$239 nightly
The price is $271
Sep 28 - Sep 29
Total with taxes and fees
2BR Apartment Near Wesleyan 102
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.

8. Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
$777 nightly
The price is $885
Sep 27 - Sep 28
Total with taxes and fees
Conference Room Rental no sleeping arrangements
A two-story house with a front porch, a garage, and a well-maintained lawn.

9. 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
9.6 out of 10, Exceptional, (19 reviews)
"The house was exactly what we were looking for, for a weekend away. Will surely book again, thank you!"
United States
Lee S.
$687 nightly
The price is $783
Sep 30 - Oct 1
Total with taxes and fees
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A living room with a dark blue sofa, a round ottoman, a coffee table, and a TV on a stand. There is a large abstract painting on the wall and a window with curtains.

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

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
$415 nightly
The price is $472
Sep 28 - Sep 29
Total with taxes and fees
Cozy basement apartment with private bathroom, kitchen and entrance.
A large, white, multi-story building with a prominent tower and a flag on top.

11. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (43 reviews)
"Very convenient location with good parking"
United States
Anonymous traveler
$214 nightly
The price is $243
Oct 27 - Oct 28
Total with taxes and fees
Walk To Goodspeed Opera House!

12. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (31 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
$224 nightly
The price is $255
Sep 29 - Sep 30
Total with taxes and fees
Family Stays: Middletown, CT
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

13. 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.
$263 nightly
The price is $281
Oct 5 - Oct 6
Total with taxes and fees
Newly Remodeled 1-BR Close to Everything yet Very Private
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

14. 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.
$266 nightly
The price is $303
Oct 6 - Oct 7
Total with taxes and fees
3 BR Apartment Near Wesleyan 201
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

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

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"This apartment was wonderful - clean, well stocked, and cute. Aside from the proximity to the train tracks (although earplugs were thoughtfully provided), the location was great - close to the highway and more importantly Dairy Queen."
United States
Becky P.
$263 nightly
The price is $281
Sep 27 - Sep 28
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

16. Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.2 out of 10, Good, (5 reviews)
"Very clean. No frills."
United States
Kristoph
$250 nightly
The price is $284
Sep 28 - Sep 29
Total with taxes and fees
Private Apt in Middletown-Wesleyan 101
A living room with a grey sofa, yellow cushions, a wooden coffee table, a TV on a stand, and a lamp on a side table.

17. 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.
$263 nightly
The price is $281
Oct 27 - Oct 28
Total with taxes and fees
Newly Remodeled with deck. Close to town center
A bedroom with a bed, a nightstand, a lamp, and a wooden wardrobe.

18. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
$531 nightly
The price is $605
Sep 27 - Sep 28
Total with taxes and fees
The Cottage by the Woods -private getaway to relax
A wooden deck with wicker furniture, white railings, and a gazebo in the background.

19. Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
Berlin
8.0 out of 10, Very good, (2 reviews)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
Soothing 2-bedroom lower-level apartment in Berlin

20. 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.
$263 nightly
The price is $281
Oct 12 - Oct 13
Total with taxes and fees
All New 1BR with tons of Charm
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

Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

10/10 Excellent
"Everything was perfect"
Mildred 1-night trip
Posted 6 hours ago
Motel 6 Wethersfield, CT - Hartford

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 $192 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 Arrigoni Winery.

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.