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

Deep River Vacation Rentals

Check prices for these dates

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

Our top choices for Deep River vacation rentals

A glass enclosure with a view of a forest interior, including a bed and a small table with items.

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
$167 nightly
The price is $192
Dec 9 - Dec 10
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
9.8 out of 10, Exceptional, (66 reviews)
"Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!"
United States
Marcy C.
$200 nightly
The price is $229
Nov 11 - Nov 12
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
$186 nightly
The price is $213
Dec 10 - Dec 11
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, (32 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
$291 nightly
The price is $332
Nov 11 - Nov 12
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

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.
$483 nightly
The price is $552
Nov 11 - Nov 12
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town
A modern kitchen with a granite island, stainless steel appliances, and a bar area with bar stools.

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.
$529 nightly
The price is $604
Dec 1 - Dec 2
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

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.
$468 nightly
The price is $535
Nov 16 - Nov 17
Total with taxes and fees
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
$341 nightly
The price is $389
Dec 1 - Dec 2
Total with taxes and fees
Westbrook Getaway-Near Beaches, Train & Shoreline
A beach with a house in the background, a clear sky, and a calm sea.

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.
$245 nightly
The price is $280
Nov 15 - Nov 16
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
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, (15 reviews)
"Cute little house with excellent amenities. Perfect for our cousins getaway!"
United States
Karol T.
$388 nightly
The price is $444
Nov 15 - Nov 16
Total with taxes and fees
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.
$1,013 nightly
The price is $1,157
Nov 12 - Nov 13
Total with taxes and fees
Charming beach home, complete with pool & cozy guest house!
A modern house with a deck, outdoor seating, and a fire pit.

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
$299 nightly
The price is $341
Nov 15 - Nov 16
Total with taxes and fees
North Fork Resort
A balcony with a view of the ocean, a lawn, and a house in the background.

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
$289 nightly
The price is $330
Nov 26 - Nov 27
Total with taxes and fees
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.
$216 nightly
The price is $247
Nov 17 - Nov 18
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A hotel lobby with a reception desk, a television mounted on the wall, a small seating area with chairs, and a window providing a view outside.

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 traveler
$81 nightly
The price is $93
Nov 11 - Nov 12
Total with taxes and fees
Cozy 2 Full Beds|Free Parking & Wifi
A bedroom with a bed, a bedside table with a tray, a TV mounted on the wall, and a window with blinds.

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
$209 nightly
The price is $239
Nov 11 - Nov 12
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
A covered patio with a glass table, white metal chairs, a green sofa, and a white metal bench.

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.
$524 nightly
The price is $599
Nov 16 - Nov 17
Total with taxes and fees
Historic New England home ,Reunions Beach pass
A modern kitchen with a central island, bar stools, and pendant lighting.

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.
$976 nightly
The price is $1,115
Nov 11 - Nov 12
Total with taxes and fees
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
$131 nightly
The price is $149
Nov 11 - Nov 12
Total with taxes and fees
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.
$223 nightly
The price is $255
Nov 11 - Nov 12
Total with taxes and fees
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

Inn at Middletown

Inn at Middletown

10/10 Excellent
"Location was great as always"
Sarah 1-night trip
Posted 1 hour ago
Inn at Middletown

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 $192 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.