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

Deep River Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Deep River 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, (197 reviews)
"Great experience and the perfect environment"
United States
Stephanie
The price is AED 496
AED 739 total
includes taxes & fees
2 Nov - 3 Nov
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
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AED 446
AED 854 total
includes taxes & fees
5 Oct - 6 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
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 traveler
The price is AED 463
AED 828 total
includes taxes & fees
22 Oct - 23 Oct
Walk To Goodspeed Opera House!
A beach with waves, a clear sky, and a sandy shore.

4. 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 AED 511
AED 1,216 total
includes taxes & fees
7 Oct - 8 Oct
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

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, (29 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is AED 579
AED 1,092 total
includes taxes & fees
7 Oct - 8 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly
A beach with a house in the background, a clear sky, and a calm sea.

6. 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
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is AED 579
AED 1,326 total
includes taxes & fees
20 Oct - 21 Oct
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
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.

7. 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 AED 459
AED 948 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

8. 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 AED 667
AED 1,808 total
includes taxes & fees
8 Oct - 9 Oct
Adorable Cottage, 5 min walk to water & town
A modern house with a deck, outdoor seating, and a fire pit.

9. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (62 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is AED 913
AED 1,043 total
includes taxes & fees
12 Oct - 13 Oct
North Fork Resort
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

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, (14 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is AED 878
AED 1,838 total
includes taxes & fees
7 Oct - 8 Oct
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A stone pier leading to a beach with houses in the background.

11. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (61 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
The price is AED 426
AED 1,011 total
includes taxes & fees
14 Oct - 15 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

12. 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 AED 853
AED 2,047 total
includes taxes & fees
4 Oct - 5 Oct
Adorable Cottage with Cottage porch, walk to water & town
A living room with a grey sofa, an orange armchair, a small round table, and a glass-top coffee table.

13. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (11 reviews)
"Great little quiet home away from home. Tom and Stacy and all the cute animals were very friendly and welcoming. Perfect place to relax after a busy day of activity."
United States
Angela A.
The price is AED 380
AED 511 total
includes taxes & fees
6 Oct - 7 Oct
The Tiny Cottage & Mini Farm
Terrace/patio

14. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is AED 621
AED 1,117 total
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

15. 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 AED 1,058
AED 2,067 total
includes taxes & fees
12 Oct - 13 Oct
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A rocky shoreline with a beach and ocean in the background.

16. 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 AED 540
AED 1,041 total
includes taxes & fees
5 Oct - 6 Oct
The Stern at Soundview · Beach+Ocean+Sunrise
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

17. 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 AED 1,119
AED 2,658 total
includes taxes & fees
2 Nov - 3 Nov
Beachside Bliss w/ Game Room, Gym & Golf Green
A cozy room with a bed, a dining table set with bowls and spoons, and a view of a lake and trees.

18. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (10 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is AED 525
AED 1,077 total
includes taxes & fees
28 Oct - 29 Oct
Lakefront Boho Tiny House
A two-story house with a front porch, a balcony, and a driveway.

19. Grey comfort room

Grey comfort room
New London
9.6 out of 10, Exceptional, (4 reviews)
"Nice place"
United States
JACQUELINE FELICIANO
The price is AED 198
AED 407 total
includes taxes & fees
21 Oct - 22 Oct
Grey comfort room
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 AED 594
AED 1,164 total
includes taxes & fees
28 Oct - 29 Oct
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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Top Deep River Hotel Reviews

Zey Hotel

Zey Hotel

10/10 Excellent
"Lots of space to sit and talk or work or catch up with friends. Only minor thing for me personally was no decaf coffee because it meant that my mom waited for me to run to get some. Great location for walking everywhere and not taking the car. And the only reason we haven’t booked every year before is we didn’t know it was there. Will be back again."
Lark 3-night trip
Posted less than an hour ago
Zey Hotel

Frequently asked questions

Can I find a vacation rental in Deep River?

Yes, we give you a choice of vacation rentals close to top local attractions in Deep River, or you can choose a secluded option if you're looking for relaxation. Deep River is known for its parks.

What's the top vacation rental in Deep River?

New Madison beach house - Ocean front- Great views- booking Summer 2026: Visitors like this Deep River 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.

How many vacation rentals are there in Deep River?

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find Connecticut Valley Railroad State Park Trail and Ivoryton Playhouse.

What’s a vacation rental in Deep River like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Deep River. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family trip.