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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (192 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
$167 nightly
The price is $192
Sep 30 - Oct 1
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, (60 reviews)
"We enjoyed our stay"
United States
JM B.
$207 nightly
The price is $234
Oct 20 - Oct 21
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

3. 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.
$392 nightly
The price is $447
Sep 28 - Sep 29
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
A large, white, multi-story building with a prominent tower and a flag on top.

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 traveler
$239 nightly
The price is $272
Sep 28 - Sep 29
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.

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)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$253 nightly
The price is $287
Oct 7 - Oct 8
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
A beach with waves, a clear sky, and a sandy shore.

6. 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.
$271 nightly
The price is $308
Sep 29 - Sep 30
Total with taxes and fees
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

7. 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.
$436 nightly
The price is $497
Sep 27 - Sep 28
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town
A beach with a house in the background, a clear sky, and a calm sea.

8. 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.
$291 nightly
The price is $331
Oct 6 - Oct 7
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A rocky shoreline with a beach and ocean in the background.

9. 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
$230 nightly
The price is $261
Sep 27 - Sep 28
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
A rocky shoreline with a clear view of the ocean and a distant shoreline with buildings.

10. 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.
$243 nightly
The price is $276
Sep 27 - Sep 28
Total with taxes and fees
Keel at Soundview · Beach+OceanView+Sunrise
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

11. 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.
$479 nightly
The price is $546
Sep 27 - Sep 28
Total with taxes and fees
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.

12. 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.
$239 nightly
The price is $272
Oct 20 - Oct 21
Total with taxes and fees
Lakefront Boho Tiny House
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.

13. 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.
$222 nightly
The price is $252
Oct 19 - Oct 20
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A stone pier leading to a beach with houses in the background.

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 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.
$232 nightly
The price is $263
Sep 30 - Oct 1
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A living room with a grey sofa, an orange armchair, a small round table, and a glass-top coffee table.

15. 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.
$124 nightly
The price is $140
Sep 29 - Sep 30
Total with taxes and fees
The Tiny Cottage & Mini Farm
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

16. 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, (13 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
$374 nightly
The price is $427
Sep 27 - Sep 28
Total with taxes and fees
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

17. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"This apartment was wonderful - clean, well stocked, and cute. Aside from the proximity to the train tracks (although earplugs were thoughtfully provided), the location was great - close to the highway and more importantly Dairy Queen."
United States
Becky P.
$263 nightly
The price is $281
Sep 27 - Sep 28
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
A two-story house with a front porch, a balcony, and a driveway.

18. Grey comfort room

Grey comfort room
New London
9.6 out of 10, Exceptional, (4 reviews)
"Nice place"
United States
JACQUELINE FELICIANO
$104 nightly
The price is $116
Sep 28 - Sep 29
Total with taxes and fees
Grey comfort room
A living room with a dark sofa, a coffee table with items, a window with a view of a house, and a bookshelf.

19. Cozy 1-bedroom apartment in peaceful Branford with AC and gym access

Cozy 1-bedroom apartment in peaceful Branford with AC and gym access
Branford
$180 nightly
The price is $204
Oct 26 - Oct 27
Total with taxes and fees
Cozy 1-bedroom apartment in peaceful Branford with AC and gym access
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

20. 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.
$466 nightly
The price is $532
Sep 28 - Sep 29
Total with taxes and fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
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

Red Roof Inn Meriden

Red Roof Inn Meriden

10/10 Excellent
"Clean and quiet. Friendly staff"
Christina 2-night trip
Posted 1 hour ago
Red Roof Inn Meriden

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.