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

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, (201 reviews)
"Great experience and the perfect environment"
United States
Stephanie
$167 nightly
The price is $192
Nov 16 - Nov 17
Total with taxes and fees
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, (62 reviews)
"We enjoyed our stay"
United States
JM B.
$183 nightly
The price is $207
Oct 21 - Oct 22
Total with taxes and fees
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
$209 nightly
The price is $237
Nov 3 - Nov 4
Total with taxes and fees
Walk To Goodspeed Opera House!
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

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, (29 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$263 nightly
The price is $297
Oct 18 - Oct 19
Total with taxes and fees
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.

5. 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.
$311 nightly
The price is $353
Oct 20 - Oct 21
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

6. 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.
$406 nightly
The price is $460
Oct 18 - Oct 19
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
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, (38 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.
$226 nightly
The price is $256
Oct 27 - Oct 28
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Terrace/patio

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
$266 nightly
The price is $304
Nov 12 - Nov 13
Total with taxes and fees
Cliffside Resort Condominiums
A stone pier leading to a beach with houses in the background.

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (64 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.
$241 nightly
The price is $272
Oct 28 - Oct 29
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

10. 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.
$486 nightly
The price is $550
Oct 20 - Oct 21
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

11. 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)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
$395 nightly
The price is $448
Oct 18 - Oct 19
Total with taxes and fees
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A living room with a sofa, armchair, coffee table, and a television.

12. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
$303 nightly
The price is $343
Oct 20 - Oct 21
Total with taxes and fees
Westbrook Getaway-Near Beaches, Train & Shoreline
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

13. 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.
$485 nightly
The price is $549
Oct 18 - Oct 19
Total with taxes and fees
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.

14. 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.
$124 nightly
The price is $139
Oct 19 - Oct 20
Total with taxes and fees
The Tiny Cottage & Mini Farm
A modern house with a deck, outdoor seating, and a fire pit.

15. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (65 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
$268 nightly
The price is $306
Oct 19 - Oct 20
Total with taxes and fees
North Fork Resort
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
8.4 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
$251 nightly
The price is $283
Oct 19 - Oct 20
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

17. 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.
$494 nightly
The price is $560
Nov 2 - Nov 3
Total with taxes and fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and lush greenery.

18. Private Guest House w/ Deck + Spectacular Views!

Private Guest House w/ Deck + Spectacular Views!
3.0 star property
Montville
10.0 out of 10, Exceptional, (3 reviews)
"The pool was amazing, the host was great, very accessible and the property was prisine. The views alone made us immediately want to come back. Very clean and well stocked. "
United States
agata
$308 nightly
The price is $354
Oct 25 - Oct 26
Total with taxes and fees
Private Guest House w/ Deck + Spectacular Views!
A cabin by a lake with a wooden exterior, a deck, and a small outdoor seating area.

19. 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.
$248 nightly
The price is $281
Nov 9 - Nov 10
Total with taxes and fees
Cozy Lakefront Tiny House
A two-story house with a front porch, a balcony, and a driveway.

20. Grey comfort room

Grey comfort room
New London
9.6 out of 10, Exceptional, (4 reviews)
$104 nightly
The price is $116
Oct 19 - Oct 20
Total with taxes and fees
Grey comfort room
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

Comfort Suites Near Casinos Norwich-Uncasville CT

Comfort Suites Near Casinos Norwich-Uncasville CT

10/10 Excellent
"Great stay. Breakfast was really good. We even received a welcome bag with snacks and water."
Angela 1-night trip
Posted 4 hours ago
Comfort Suites Near Casinos Norwich-Uncasville CT

Find out more about Deep River

Everything you need to know about Deep River vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Deep River vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Deep River vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Deep River vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Deep River. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Deep River in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $116 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Deep River rentals

At Expedia, we put the best Deep River vacation 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 Deep River 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 Deep River vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Deep River. 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

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.