Cuddebackville Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Cuddebackville vacation rentals

A spacious kitchen with wooden cabinets, a central island, and a dining area with chairs.

1. Serene Rustic Retreat with Lake

Serene Rustic Retreat with Lake
Cuddebackville
9.6 out of 10, Exceptional, (10 reviews)
"Amazing stay and beautiful home!"
United States
Koby A.
The price is CA $294
CA $729 total
includes taxes & fees
Nov 9 - Nov 10
Serene Rustic Retreat with Lake
A spacious living area with a fireplace, dining table, and seating arrangements.

2. Fantastic 5-bedroom country house w/ private access to neversink river near NYC

Fantastic 5-bedroom country house w/ private access to neversink river near NYC
Cuddebackville
8.0 out of 10, Very good, (2 reviews)
"Great communication, location/scenery was gorgeous"
United States
Lisa R.
The price is CA $489
CA $1,080 total
includes taxes & fees
Nov 9 - Nov 10
Fantastic 5-bedroom country house w/ private access to neversink river near NYC
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

3. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
Wurtsboro
9.6 out of 10, Exceptional, (10 reviews)
"Clean, cozy, relaxing vibes"
United States
Daniel S.
The price is CA $231
CA $471 total
includes taxes & fees
Nov 8 - Nov 9
Hike & Fish: Outdoor Retreat Near Trails
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

4. Columbus Suites

Columbus Suites
3.0 star property
Middletown
6.4 out of 10, (21 reviews)
"My worst experience ever staying at the hotel no communication locked out at the sleep in my car. I would never recommend anybody to stay there. The bed is horrible no curtains window basically nothing nice to say about that property. Sorry."
United States
Edwin
The price is CA $77
CA $190 total
includes taxes & fees
Nov 9 - Nov 10
Columbus Suites
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

5. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is CA $296
CA $480 total
includes taxes & fees
Dec 7 - Dec 8
Hike & Fish: Outdoor Retreat Near Trails
A room with a sloped ceiling, wooden beams, and two windows with curtains.

6. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
8.8 out of 10, Excellent, (23 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
The price is CA $99
CA $150 total
includes taxes & fees
Nov 10 - Nov 11
Trails Head Tiny House
A small black cabin with a metal roof, surrounded by a grassy area and trees.

7. Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (125 reviews)
"Great location being right at the trailhead for hiking."
United States
Tonne
The price is CA $170
CA $281 total
includes taxes & fees
Nov 10 - Nov 11
Trails Head Cabin
An open door leading to a deck with outdoor furniture and a stone wall.

8. Hello Small Stone

Hello Small Stone
Middletown
9.8 out of 10, Exceptional, (7 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is CA $184
CA $511 total
includes taxes & fees
Nov 8 - Nov 9
Hello Small Stone
A bedroom with a wooden floor, a bed with white bedding, a dresser, and an open door leading to a bathroom.

9. Cozy Huguenot Hideaway

Cozy Huguenot Hideaway
Huguenot
The price is CA $353
CA $799 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Huguenot Hideaway
A covered deck with outdoor seating and string lights.

10. Cozy River Valley Family Retreat w/ Fireplace, Games & Serene Deck

Cozy River Valley Family Retreat w/ Fireplace, Games & Serene Deck
Sparrow Bush
9.4 out of 10, Exceptional, (9 reviews)
"Great stay, host was very responsive, would definitely stay again! "
United States
Shriraj S.
The price is CA $286
CA $353 total
includes taxes & fees
Nov 9 - Nov 10
Cozy River Valley Family Retreat w/ Fireplace, Games & Serene Deck
Beautiful Montague sunset

11. Rare River Views & Access, Cabin by Eden Islands

Rare River Views & Access, Cabin by Eden Islands
Montague
8.8 out of 10, Excellent, (18 reviews)
"Host was accessible and very nice location to enjoy what nature brings."
United Kingdom
Rohan L.
The price is CA $154
CA $213 total
includes taxes & fees
Dec 1 - Dec 2
Rare River Views & Access, Cabin by Eden Islands
Living room (3)

12. Scenic Views & River Access, Cozy River Home

Scenic Views & River Access, Cozy River Home
Montague
9.2 out of 10, Wonderful, (20 reviews)
"This house was very clean and spacious! Having access to the river makes this place very special. The host was very communicative and response to requests if needed. I was very happy with my stay at this Tri-State property. It's very easy to get to and the directions are very clear."
United States
Elizabeth W.
The price is CA $165
CA $224 total
includes taxes & fees
Dec 7 - Dec 8
Scenic Views & River Access, Cozy River Home
Patio (2)

13. Forest and River Side Tranquil House

Forest and River Side Tranquil House
Montague
7.6 out of 10, Good, (21 reviews)
"The location of the house was great and the surrounding neighborhood and wooded area was really nice. I would suggest to the owner to provide a bit more kitchenware in the kitchen and possibly a bit more furniture in the living room. Overall, my family and i had a good time."
United States
Anonymous traveller
The price is CA $165
CA $224 total
includes taxes & fees
Dec 6 - Dec 7
Forest and River Side Tranquil House
A house with a stone staircase leading to a wooden deck with string lights.

14. Breathtaking River Views · The Hawks Nest Cabin

Breathtaking River Views · The Hawks Nest Cabin
Glen Spey
10.0 out of 10, Exceptional, (11 reviews)
"Nice sized cabin for a relaxing weekend away. We enjoyed the views from the deck. We spent time on the river. Highly recommend if you want to be near the Delaware River!"
United States
Jessica G.
The price is CA $303
CA $621 total
includes taxes & fees
Nov 8 - Nov 9
Breathtaking River Views · The Hawks Nest Cabin
A cozy living area with a brick fireplace, a blue sofa, and a red chair.

15. Peaceful 3-Bedroom Log Cabin Retreat in the Heart of Idyllic Sparrow Bush NY

Peaceful 3-Bedroom Log Cabin Retreat in the Heart of Idyllic Sparrow Bush NY
Sparrow Bush
10.0 out of 10, Exceptional, (4 reviews)
"Wonderful property!!"
United States
Kathryn D.
The price is CA $484
CA $937 total
includes taxes & fees
Nov 10 - Nov 11
Peaceful 3-Bedroom Log Cabin Retreat in the Heart of Idyllic Sparrow Bush NY
A modern living room with a stone fireplace, a flat-screen TV, and a sliding glass door leading to an outdoor area.

16. Beaver Lake Escape

Beaver Lake Escape
Rock Hill
9.6 out of 10, Exceptional, (44 reviews)
"It was amazing quiet, clean, in a great location. Will go back again."
United States
GinaMarie C.
The price is CA $208
CA $324 total
includes taxes & fees
Nov 10 - Nov 11
Beaver Lake Escape
A wooden staircase leading to a garden area with a pathway, rocks, and plants.

17. 3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
Forestburgh
9.6 out of 10, Exceptional, (16 reviews)
"5 stars across the board! Super communicative host, even offered to change cleaning crew schedule to accommodate our needs. There is a beautiful creek going through the back yard. It’s lovely. I feel like pictures dont do it justice. Definitely a wonderful experience."
United States
Dea
The price is CA $252
CA $480 total
includes taxes & fees
Nov 9 - Nov 10
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
A log cabin with a deck, stone foundation, and a green umbrella.

18. Secluded Luxury Catskills Log Cabin - 4BR, Fireplace & Fire Pit, Sleeps 8

Secluded Luxury Catskills Log Cabin - 4BR, Fireplace & Fire Pit, Sleeps 8
Glen Spey
10.0 out of 10, Exceptional, (4 reviews)
"beautiful cabin!"
United States
liah w.
The price is CA $568
CA $992 total
includes taxes & fees
Nov 12 - Nov 13
Secluded Luxury Catskills Log Cabin - 4BR, Fireplace & Fire Pit, Sleeps 8
An outdoor deck with a wooden table and chairs, a grill, and a hot tub.

19. Luxury Retreat w/ Hot Tub - near Bethel Woods!

Luxury Retreat w/ Hot Tub - near Bethel Woods!
Forestburgh
10.0 out of 10, Exceptional, (9 reviews)
"This was an excellent property.It was clean, well stocked and beautiful. The host was attentive and available. It was really a wonderful stay."
United States
mary
The price is CA $462
CA $901 total
includes taxes & fees
Nov 8 - Nov 9
Luxury Retreat w/ Hot Tub - near Bethel Woods!
A small cabin with a porch, surrounded by dense forest and a clear night sky with a visible moon.

20. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.8 out of 10, Exceptional, (6 reviews)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
The price is CA $210
CA $305 total
includes taxes & fees
Nov 30 - Dec 1
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
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 Cuddebackville Hotel Reviews

A modern dining area with a large fish tank, sofas, and wooden tables and chairs.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown

10/10 Excellent

We enjoyed the room, clean, helpful staff. The kids loved the pool and breakfast
Canada
Tawnia
Reviewed October 13, 2026
Sleep Inn & Suites Middletown - Goshen

Find out more about Cuddebackville

Everything you need to know about Cuddebackville 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 Cuddebackville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 Cuddebackville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cuddebackville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cuddebackville. 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 Cuddebackville vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cuddebackville vacation rentals we have selected for you start as low as CA $77 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cuddebackville rentals

At Expedia, we put the best Cuddebackville 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 Cuddebackville 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 Cuddebackville 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 Cuddebackville. 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

Are there vacation rentals in Cuddebackville?

Yes, we have vacation rentals in Cuddebackville close to Oakland Valley Race Park, or you can go with a more remote option if you want a relaxing stay.

What's the top vacation rental in Cuddebackville?

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This vacation home rental outside of Cuddebackville is located on a lake and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Cuddebackville?

Choose from 3 Expedia vacation rentals in Cuddebackville for a memorable vacation.

What can I see and do in Cuddebackville?

Enjoy the outdoors at Neversink River and Delaware and Hudson Canal County Park, or simply take in cultural attractions like Neversink Valley Area Museum and Neversink Valley Museum of History & Innovation. In the larger area, you’ll find Oakland Valley Race Park and The Hawk's Nest Lookout.

What are vacation rentals like in Cuddebackville?

Vacation rentals are private properties you can book for several days or more in Cuddebackville. Vacation rentals offer extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.