Deep River Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Deep River holiday rentals

A cabin surrounded by a natural forest setting with a fire pit and picnic table.

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, (222 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is HK$1,059
HK$1,579 total
includes taxes & fees
13 Dec - 14 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

2. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (67 reviews)
"Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!"
United States
Marcy C.
The price is HK$1,183
HK$1,986 total
includes taxes & fees
19 Nov - 20 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
A white door with a window, set in a green brick wall.

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 HK$894
HK$1,582 total
includes taxes & fees
10 Dec - 11 Dec
Walk To Goodspeed Opera House!
A bench by a calm lake with boats docked in the background.

4. 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, (32 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is HK$1,589
HK$2,676 total
includes taxes & fees
18 Nov - 19 Nov
The gardners Cottage 1 mile from long Island Sound - pet friendly
A living room with a beige sofa, a wooden coffee table, and a dining area with a small table and chairs. There is a large window with sheer curtains, a framed fish picture on the wall, and a potted plant.

5. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and comfortable"
United States
Francine F.
The price is HK$1,912
HK$4,289 total
includes taxes & fees
13 Nov - 14 Nov
Adorable Cottage with Cottage porch, walk to water & town
A beach with clear skies and calm water.

6. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (4 reviews)
"Very lovely home! We very much enjoyed our stay and hope to be back again!"
United States
Morgan M.
The price is HK$1,886
HK$4,775 total
includes taxes & fees
1 Dec - 2 Dec
Beachside Bliss w/ Game Room, Gym & Golf Green
A porch with a blue door, white columns, and a stone floor.

7. 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.
The price is HK$2,330
HK$4,299 total
includes taxes & fees
16 Nov - 17 Nov
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

8. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is HK$2,372
HK$3,142 total
includes taxes & fees
2 Dec - 3 Dec
Westbrook Getaway-Near Beaches, Train & Shoreline
A wooden boardwalk leading to a sandy beach with people sitting and standing, overlooking the ocean.

9. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is HK$1,165
HK$2,248 total
includes taxes & fees
15 Nov - 16 Nov
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A covered outdoor seating area with a wicker sofa and a coffee table, surrounded by greenery.

10. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (15 reviews)
"Cute little house with excellent amenities. Perfect for our cousins getaway!"
United States
Karol T.
The price is HK$1,647
HK$3,566 total
includes taxes & fees
15 Nov - 16 Nov
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A modern living room with a large TV, white cabinetry, and a view of the outdoors.

11. Charming beach home, complete with pool & cozy guest house!

Charming beach home, complete with pool & cozy guest house!
Clinton
9.8 out of 10, Exceptional, (56 reviews)
"Beautiful, open and clean. Perfect for a family stay!"
United States
Juliana A.
Charming beach home, complete with pool & cozy guest house!
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

12. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is HK$2,521
HK$2,880 total
includes taxes & fees
15 Nov - 16 Nov
North Fork Resort
Terrace/patio

13. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is HK$1,507
HK$2,592 total
includes taxes & fees
26 Nov - 27 Nov
Cliffside Resort Condominiums
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.

14. 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, (40 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$981
HK$1,991 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A hotel reception area with a receptionist, a guest, and a child.

15. Cozy 2 Full Beds|Free Parking & Wifi

Cozy 2 Full Beds|Free Parking & Wifi
Niantic
10.0 out of 10, Exceptional, (55 reviews)
"Close to local spots, good value for what you get."
United States
Anonymous traveller
The price is HK$629
HK$723 total
includes taxes & fees
16 Nov - 17 Nov
Cozy 2 Full Beds|Free Parking & Wifi
A beach with waves, a clear sky, and a sandy shore.

16. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.4 out of 10, Very good, (6 reviews)
"If you are looking for a place to sleep, this place is ok. No place to sit down or put anything down. Just a bed and an old beat up tiny side table. Refrigerator is tiny, needed to be cleaned and defrosted. Stains in the bathroom ceiling tiles and the smell of Marijuana at night. Hot plate and microwave present but did not use. The entryway and stairs were dirty and could use a coat of paint and trim. The beach was the highlight and a very short walk. Definitely not worth the $$$ we paid."
United States
Janine
The price is HK$1,046
HK$1,938 total
includes taxes & fees
15 Nov - 16 Nov
The Stern at Soundview · Beach+Ocean+Sunrise
A kitchen with a wooden table, chairs, a microwave, and a sink.

17. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.4 out of 10, Exceptional, (93 reviews)
"The location of this place is best!"
United States
Dr. Maureen C.
The price is HK$2,354
HK$4,817 total
includes taxes & fees
16 Nov - 17 Nov
Historic New England home ,Reunions Beach pass
A two-story house with a front porch, large windows, and a well-maintained lawn.

18. 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, (35 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$5,687
HK$8,965 total
includes taxes & fees
18 Nov - 19 Nov
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A pond with rocks and a dog in the background.

19. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (14 reviews)
"Love love love this place. A very unique setting on a little farm and the cabin was great. Everything ya need. A gorgeous setting. Tom, the owner is great. Will. Be. Back."
United States
Paul
The price is HK$953
HK$1,190 total
includes taxes & fees
16 Nov - 17 Nov
The Tiny Cottage & Mini Farm
A cabin by a lake with a wooden exterior, a deck, and a small outdoor seating area.

20. Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (5 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is HK$1,159
HK$2,292 total
includes taxes & fees
29 Nov - 30 Nov
Cozy Lakefront Tiny House
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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Find out more about Deep River

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

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Look no further and take a look at our great range of rental properties in Deep River!

Frequently Asked Questions

Can I find a holiday rental in Deep River?

Yes, there are holiday rentals close to the most popular sights in Deep River, or you can select a more secluded option if you're looking for a relaxing stay. Deep River is known for its parks.

What are some of the best holiday rentals that Deep River has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of Deep River 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 Deep River?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Deep River stay.

What’s there to see and do in Deep River?

Connecticut River and Plattwood Park are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Connecticut Valley Railroad State Park Trail and Ivoryton Playhouse.

What’s a holiday rental in Deep River like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Deep River. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.