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Middle Haddam Holiday Rentals

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Check prices for these dates

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

Our top choices for Middle Haddam holiday rentals

A compact kitchen with wooden walls, a window with a view of greenery, a built-in dishwasher, and a sink.

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, (191 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is HK$1,091
HK$1,615 total
includes taxes & fees
24 Sept - 25 Sept
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.
The price is HK$1,051
HK$2,097 total
includes taxes & fees
20 Oct - 21 Oct
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.
The price is HK$1,670
HK$3,874 total
includes taxes & fees
7 Oct - 8 Oct
#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.
The price is HK$1,251
HK$2,693 total
includes taxes & fees
29 Sept - 30 Sept
#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.
The price is HK$5,098
HK$8,095 total
includes taxes & fees
25 Sept - 26 Sept
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.
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.
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
The price is HK$5,647
HK$7,302 total
includes taxes & fees
5 Oct - 6 Oct
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.
The price is HK$3,721
HK$6,588 total
includes taxes & fees
28 Sept - 29 Sept
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
The price is HK$1,306
HK$3,918 total
includes taxes & fees
6 Oct - 7 Oct
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 traveller
The price is HK$1,012
HK$1,795 total
includes taxes & fees
24 Sept - 25 Sept
Walk To Goodspeed Opera House!

12. 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.
The price is HK$1,185
HK$2,168 total
includes taxes & fees
13 Oct - 14 Oct
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.
The price is HK$926
HK$2,304 total
includes taxes & fees
5 Oct - 6 Oct
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.
The price is HK$1,020
HK$2,507 total
includes taxes & fees
29 Sept - 30 Sept
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
9.0 out of 10, Wonderful, (14 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.
The price is HK$926
HK$2,288 total
includes taxes & fees
24 Sept - 25 Sept
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
The price is HK$1,051
HK$2,551 total
includes taxes & fees
28 Sept - 29 Sept
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.
The price is HK$926
HK$2,288 total
includes taxes & fees
25 Sept - 26 Sept
Newly Remodeled with deck. Close to town center
A bedroom with a bed, a painting of birds, a window with shutters, and a patterned rug.

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is HK$2,118
HK$5,022 total
includes taxes & fees
26 Sept - 27 Sept
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.
The price is HK$1,010
HK$2,548 total
includes taxes & fees
28 Sept - 29 Sept
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.
The price is HK$926
HK$2,225 total
includes taxes & fees
21 Oct - 22 Oct
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Nice room,"
Russell 1-night trip
Posted 18 hours ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Middle Haddam

Search for holiday rentals in Middle Haddam on Expedia! You can easily find your home rentals, villas, holiday apartments in Middle Haddam using one of the methods below:

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Frequently asked questions

Are there holiday rentals in Middle Haddam?

Yes, there are holiday rentals close to the most popular sights in Middle Haddam, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middle Haddam has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of Middle Haddam is located on the beach, and has a balcony, a BBQ 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 that 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 wider area, you’ll find Hurd State Park and Arrigoni Winery.

What are holiday rentals like in Middle Haddam?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middle Haddam. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.