A forested hillside with autumn foliage.

East Hampton Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for East Hampton holiday 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, (203 reviews)
"Great experience and the perfect environment"
United States
Stephanie
The price is AU$276
includes taxes & fees
16 Nov - 17 Nov
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, (39 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 AU$379
includes taxes & fees
27 Oct - 28 Oct
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, (43 reviews)
"Very convenient location with good parking"
United States
Anonymous traveller
The price is AU$341
includes taxes & fees
3 Nov - 4 Nov
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
9.6 out of 10, Exceptional, (4 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 AU$422
includes taxes & fees
19 Oct - 20 Oct
2BR Apartment Near Wesleyan 301
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

5. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (7 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is AU$409
includes taxes & fees
18 Oct - 19 Oct
2BR Apartment Near Wesleyan 102
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.

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

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is AU$682
includes taxes & fees
18 Oct - 19 Oct
Cozy basement apartment with private bathroom, kitchen and entrance.
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

7. 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 AU$487
includes taxes & fees
17 Nov - 18 Nov
3 BR Apartment Near Wesleyan 201
Veterans Park, near the house

8. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (33 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is AU$382
includes taxes & fees
17 Nov - 18 Nov
Family Stays: Middletown, CT
A modern kitchen with white cabinets, a stainless steel refrigerator, a dining area with two chairs, and a coffee machine.

9. “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.
The price is AU$417
includes taxes & fees
31 Oct - 1 Nov
“3BR Home Near Wesleyan & Downtown Middletown
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

10. 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 AU$420
includes taxes & fees
20 Oct - 21 Oct
Private Apt in Middletown-Wesleyan 101
A modern living room with a sofa, a dining table, and a massage chair.

11. #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 AU$809
includes taxes & fees
2 Nov - 3 Nov
#29 - Modern 5 Bedroom/2 Bath
Stairwell

12. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
The price is AU$399
includes taxes & fees
3 Nov - 4 Nov
Private Apartment in Berlin
A kitchen with a sink, wooden shelves, a decorative sign, and a vase with flowers.

13. Privet Farm cottage with AC and Deck in charming Salem Connecticut

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
9.0 out of 10, Wonderful, (4 reviews)
"The place was perfect! So much bigger and nicer in person!!!!! Well appointed very cozy! Clean!!!!! Very pet friendly! Great shower!"
United States
Kellie
The price is AU$454
includes taxes & fees
18 Oct - 19 Oct
Privet Farm cottage with AC and Deck in charming Salem Connecticut
A lakeside view with a sandy beach, kayaks, and a 'No Dogs' sign.

14. 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, (49 reviews)
"Very peaceful and beautiful area. Well needed relaxing time. Highly recommend! Also Host was exceptional and attentive."
United States
Melissa
The price is AU$364
includes taxes & fees
18 Oct - 19 Oct
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A living room with a grey sofa, an orange armchair, a small round table, and a glass-top coffee table.

15. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (13 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is AU$203
includes taxes & fees
20 Oct - 21 Oct
The Tiny Cottage & Mini Farm
A wooden deck with a staircase leading to a covered area with chairs.

16. Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (6 reviews)
"the place was clean bed was nice"
United States
Jonathan
The price is AU$230
includes taxes & fees
19 Oct - 20 Oct
Humble Abode #2
A living room with a dining area, a TV, and a large window with a view of buildings.

17. Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.4 out of 10, Exceptional, (8 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is AU$322
includes taxes & fees
18 Oct - 19 Oct
Central Chic Pad - with Free Parking, Heat & AC
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

18. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable with easy communication with host I recommend this unit to all who want to visit Wallingford or who desire to take the train to ny or Boston etc"
United States
DAVID B.
The price is AU$418
includes taxes & fees
20 Oct - 21 Oct
All New Studio apartment in center of town
A blue sofa with plaid pillows, a glass coffee table with a white flower centerpiece, and two potted plants.

19. Premier League Pad - with Free Parking, Heat & AC

Premier League Pad - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (3 reviews)
"Perfect place to stay if you need to stay in Manchester. The apartment was so clean and accommodating. The host was very easy to communicate with! I would gladly stay here again!"
United States
Corey J.
The price is AU$364
includes taxes & fees
18 Oct - 19 Oct
Premier League Pad - with Free Parking, Heat & AC
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

20. Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (30 reviews)
"Was a great stay"
United States
John S.
The price is AU$442
includes taxes & fees
21 Oct - 22 Oct
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
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 East Hampton Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Worn furnishings but room was clean and staff was helpful, accommodated my check in after midnight."
Neal 3-night trip
Posted 2 hours ago
Pier Blue Inn Old Saybrook - Essex

Find out more about East Hampton

Everything you need to know about East Hampton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the East Hampton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 East Hampton holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

East Hampton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in East Hampton. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A East Hampton holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of East Hampton holiday rentals we have selected for you start as low as AU$276 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on East Hampton rentals

At Expedia, we put the best East Hampton holiday 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 East Hampton 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 East Hampton holiday.

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

Explore a world of travel with Expedia

Frequently asked questions

Are there holiday rentals in East Hampton?

Yes, there are holiday rentals close to the most popular sights in East Hampton, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in East Hampton. Make sure you have time to check out the waterfront while you're in the area.

What are some of the best holiday rentals that East Hampton has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of East Hampton 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.

How many holiday rentals are there in East Hampton?

With 15 Expedia holiday rentals, you're guaranteed to find just the right place for your East Hampton stay.

What’s there to see and do in East Hampton?

Connecticut River and Lake Pocotopaug are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Machimoodus State Park and Comstock Bridge.

What’s a holiday rental in East Hampton like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in East Hampton. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.