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

Holiday Rentals in Deep River

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Our top choices for Deep River holiday rentals

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)
"ABSOLUTELY BEAUTIFUL AND SERENE STAY . WE REALLY ENJOYED OUR STAY !"
United States
Melissa
The price is €187
includes taxes & fees
1 Nov - 2 Nov
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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 €209
includes taxes & fees
26 Oct - 27 Oct
1-bedroom cottage with Grove Beach 🏖️ access.

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 traveller
The price is €276
includes taxes & fees
13 Oct - 14 Oct
Walk To Goodspeed Opera House!

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 €294
includes taxes & fees
7 Oct - 8 Oct
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

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 €271
includes taxes & fees
13 Oct - 14 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly

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 €318
includes taxes & fees
20 Oct - 21 Oct
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

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 €229
includes taxes & fees
19 Oct - 20 Oct
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

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 €430
includes taxes & fees
7 Oct - 8 Oct
Adorable Cottage, 5 min walk to water & town

9. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (61 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is €269
includes taxes & fees
4 Oct - 5 Oct
North Fork Resort

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.
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

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 €240
includes taxes & fees
14 Oct - 15 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!

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 €472
includes taxes & fees
2 Oct - 3 Oct
Adorable Cottage with Cottage porch, walk to water & town

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 €127
includes taxes & fees
6 Oct - 7 Oct
The Tiny Cottage & Mini Farm

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 €268
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums

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 €491
includes taxes & fees
12 Oct - 13 Oct
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

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 €266
includes taxes & fees
5 Oct - 6 Oct
The Stern at Soundview · Beach+Ocean+Sunrise

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 €678
includes taxes & fees
7 Oct - 8 Oct
Beachside Bliss w/ Game Room, Gym & Golf Green

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 €265
includes taxes & fees
21 Oct - 22 Oct
Lakefront Boho Tiny House

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 €102
includes taxes & fees
5 Oct - 6 Oct
Grey comfort room

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 €291
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

Find out more about Deep River

Everything you need to know about Deep River holiday rentals

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

Deep River holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Deep River holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Deep River holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Deep River rentals

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

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. 

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.