A forest stream with a small waterfall surrounded by rocks and trees.

Deep River Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Deep River holiday rentals

Private kitchen

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, (189 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is HK$1,012
HK$1,525 total
includes taxes & fees
22 Sept - 23 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Interior

2. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is HK$1,299
HK$3,700 total
includes taxes & fees
20 Sept - 21 Sept
Adorable Cottage, 5 min walk to water & town
Dining

3. 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)
"Great host and property"
United States
Kevin K.
The price is HK$1,624
HK$4,112 total
includes taxes & fees
20 Sept - 21 Sept
Adorable Cottage with Cottage porch, walk to water & town
Exterior

4. 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$1,028
HK$1,813 total
includes taxes & fees
22 Sept - 23 Sept
Walk To Goodspeed Opera House!
Coffee/tea maker, fridge, microwave, oven

5. 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.
The price is HK$1,373
HK$2,436 total
includes taxes & fees
7 Oct - 8 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly
1 bedroom, desk, iron/ironing board, travel cot

6. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (59 reviews)
"We enjoyed our stay"
United States
JM B.
The price is HK$946
HK$1,801 total
includes taxes & fees
6 Oct - 7 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
Beach

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$2,278
HK$5,532 total
includes taxes & fees
20 Oct - 21 Oct
Beachside Bliss w/ Game Room, Gym & Golf Green
Interior

8. 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$2,259
HK$4,265 total
includes taxes & fees
28 Sept - 29 Sept
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Beach nearby

9. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
The price is HK$1,244
HK$2,770 total
includes taxes & fees
24 Sept - 25 Sept
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Dining

10. Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Old Saybrook
9.8 out of 10, Exceptional, (41 reviews)
"Enjoyed our stay"
United States
Nicole L.
The price is HK$4,315
HK$7,308 total
includes taxes & fees
24 Sept - 25 Sept
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
TV, books

11. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (95 reviews)
"Great cottage on the Sound!"
United States
David S.
Direct waterfront renovated cottage.
Interior

12. 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, (31 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$5,099
HK$8,096 total
includes taxes & fees
21 Sept - 22 Sept
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Outdoor dining

13. Lakeside Bliss

Lakeside Bliss
East Lyme
9.6 out of 10, Exceptional, (31 reviews)
"Lovely house - excellently equipped and fun decor. The owner was gracious and flexible and the location is beautiful. "
United States
Brenda M.
The price is HK$2,818
HK$4,305 total
includes taxes & fees
27 Sept - 28 Sept
Lakeside Bliss
Beach nearby

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

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.0 out of 10, Very good, (5 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$1,021
HK$2,058 total
includes taxes & fees
20 Sept - 21 Sept
The Stern at Soundview · Beach+Ocean+Sunrise
Flat-screen TV

15. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (56 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is HK$2,351
HK$2,686 total
includes taxes & fees
18 Oct - 19 Oct
North Fork Resort
Exterior

16. 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$1,338
HK$2,604 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Lakefront Tiny House
Terrace/patio

17. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (292 reviews)
"Great place!"
United States
Christine
The price is HK$2,160
HK$3,338 total
includes taxes & fees
5 Oct - 6 Oct
Cliffside Resort Condominiums
Smart TV, fireplace, books, music library

18. 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
Outdoor dining

19. Direct Lakefront - Stunning Views and Panoramic Sunsets

Direct Lakefront - Stunning Views and Panoramic Sunsets
East Lyme
10.0 out of 10, Exceptional, (2 reviews)
"We really enjoyed our stay. It was very peaceful and relaxing. The view of the lake from sunrise to sunset was truly breathtaking."
United States
Chuck T.
The price is HK$1,631
HK$3,416 total
includes taxes & fees
20 Sept - 21 Sept
Direct Lakefront - Stunning Views and Panoramic Sunsets
Beach nearby

20. Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"Very peaceful community. Great accommodations!"
United States
Joseph O.
The price is HK$1,304
HK$2,414 total
includes taxes & fees
24 Sept - 25 Sept
Keel at Soundview · Beach+OceanView+Sunrise
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 Deep River Hotel Reviews

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

8/10 Good
"Convenient location, comfortable and clean, nice breakfast, reasonable price...one small thing needs touch up on ceiling paint in bathroom and main area."
Dawna 1-night trip
Posted 8 hours ago
Hyatt Place Uncasville - Casino Area

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:

  • View our selection of featured holiday rentals in Deep River
  • Use the map to find apartments and other holiday homes in the Deep River neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Deep River while they last

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.