Town of Rockland Vacation Rentals from CA $227: Short-Term Rentals for 2026

Our top choices for Town of Rockland vacation rentals

A gym with a weight machine, a mirror, and a door.

1. Charming 1 bedroom apartment with AC in quaint Roscoe

Roscoe

"Nice venue and owner is very nice and lives in the house that is attached. He needs to make some adjustments. We hope this is helpful to him. Most important, he absolutely needs to dump the mattress that is on the bed. It is not supportive. It's way too soft and I woke up each morning with a very hurting back. Other things: need to get a non slip mat for the shower. Needs to leave written instructions with the wifi code. Needs to add tissue boxes. Needs to add an extension cord so that you can...

Lawrence

CA $218 total

includes taxes & fees

Nov 7 - Nov 8

A snow-covered landscape with a building labeled "Trout Town Inn" and a covered outdoor area with trees.

2. Catskills Adventures

Roscoe

kevin

CA $280 total

includes taxes & fees

Nov 7 - Nov 8

A spacious room with a spiral staircase, a wooden bench, a table with a lamp, and a view of the outdoors through a glass door.

3. Tiny Home * Big Mountain View’s * Cozy Fireplace

Parksville

Anonymous traveller

CA $636 total

includes taxes & fees

Nov 10 - Nov 11

Start your morning with coffee on the covered deck, surrounded by the quiet forest.

4. The Roscoe Rise - Hot Tub Sauna Fire Pit MCM Cabin

Roscoe

CA $724 total

includes taxes & fees

Nov 10 - Nov 11

A wooden deck with a metal railing overlooking a river and forested area.

5. Waterfront property, perfect winter getaway, directly on the Willowemoc!

Livingston Manor

Daniel D.

CA $531 total

includes taxes & fees

Nov 7 - Nov 8

A spacious living room with a high ceiling, large windows, a sofa, a bench, and a telescope.

6. Hot Tub, Private Dock, Quiet Lake Home

Livingston Manor

Dave

CA $1,314 total

includes taxes & fees

Nov 9 - Nov 10

A wooden building with a deck, outdoor seating, and a visible chimney emitting smoke.

7. Welcome Families and Friends to the Home of Laughter and More Laughter

Livingston Manor

CA $724 total

includes taxes & fees

Nov 17 - Nov 18

A tent with a mesh screen, set on a wooden platform, surrounded by greenery.

8. CABIN TENT ON WORKING RANCH NEAR BETHEL WOODS

Parksville

"My husband and I were pretty excited about glamping for the first time. Until we got there. We arrived at the ranch and no one seemed to know anything about whete we were staying until we finally found the host, Rose. Rose was nice person, but had no idea who we were or if we were the ones who were staying in one of the tents. She did not even ask for our names, but directed us to one of the tents. What we found was disgraceful. The two beds were messily made with dirty, looking blankets and...

Grail

CA $147 total

includes taxes & fees

Nov 7 - Nov 8

A cabin surrounded by a natural forest setting with a fire pit and picnic table.

9. Postcard Cabins Western Catskills, Outdoor Collection by Marriott Bonvoy

Roscoe

Tyrese

CA $257 total

includes taxes & fees

Dec 7 - Dec 8

10. Suites on Main

Margaretville

"You get what you pay for - cheap, not value. Spent the first 2 hours cleaning because it was barely touched - even dining table and chairs had crumbs and spill stains. The coffee maker was black inside the water compartment. I had to pick up silverware and dish soap from the dollar store because there was only 2 forks and spoons for a place advertised for 6 and no dish soap to clean dishes. I’m confident my cleaning and items I left behind for the next guests will be reimbursed by karma. Oh,...

Jonathan

CA $196 total

includes taxes & fees

Nov 8 - Nov 9

A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

11. Starlite Motel

Big Indian

Stephen

CA $227 total

includes taxes & fees

Nov 12 - Nov 13

A modern living room with a sofa, coffee table, and a fireplace.

12. Charming Swan Lake Retreat w/ Hot Tub & Deck

Swan Lake

Debra

CA $585 total

includes taxes & fees

Nov 8 - Nov 9

A tent set up in a forest with a campfire in front.

13. Turey Forest Camping Near Bethel Woods - 15 minutes to Bethel Woods, Casino,

Harris

"Taino wood was a great place for camping. Chantel and her husband Jesse are great host and are very welcoming and kind. Nice place to enjoy with your family in the nature. There were many tent sites inside their woods and we occupied the site called:Turey. We set up 3 tents (two 4-people tents and one 6-people tent). There was a firepit we used to cook food and Chantel and Jesse lend us a pot to cook. Before leaving Chantel, Jesse and a few of their friends sang indigenous songs and played...

Lissette

CA $134 total

includes taxes & fees

Nov 16 - Nov 17

A wooden deck with a table and chairs, overlooking a snowy landscape with bare trees.

14. Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

Shandaken

afsoon p.

CA $265 total

includes taxes & fees

Dec 1 - Dec 2

A cabin with a deck, a fire pit, and outdoor seating.

15. Off-Grid Tiny Cabin with Cozy Vintage Charm

Bovina

LILLIAN R.

CA $380 total

includes taxes & fees

Nov 8 - Nov 9

A fire pit with logs, surrounded by rocks and gravel, with two red chairs and a tree stump nearby.

16. Roscoe Cottage Pet Friendly

Roscoe

Darwin

CA $331 total

includes taxes & fees

Nov 16 - Nov 17

A house with a dock by a lake, surrounded by trees and a clear sky.

17. Lakeview Cabin Duplex

Lake Huntington

melissa m.

CA $312 total

includes taxes & fees

Nov 10 - Nov 11

A residential house with a pathway leading to the front door, surrounded by a well-maintained lawn and trees.

18. New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi

Hurleyville

Holly L.

CA $323 total

includes taxes & fees

Nov 8 - Nov 9

A log cabin with a wooden door, a window, a bench, and a table.

19. Handcrafted Riverfront Cabin on 10 acres

Starlight

Joe M.

CA $490 total

includes taxes & fees

Nov 9 - Nov 10

A house surrounded by trees and a river.

20. Callicoon Creek Farmhouse

Callicoon

Tom B.

CA $492 total

includes taxes & fees

Nov 9 - Nov 10

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Top Town of Rockland Hotel Reviews

Hampton Inn Monticello

10/10 Excellent

"Great stay; clean room; close to food options"

Kenoza Lake View Manor

10/10 Excellent

"Kenoza Lake View Manor is a truly exceptional property, lovingly maintained and adorned with beautiful period furnishings that reflect the charm and elegance of a bygone era. Every room showcases the care, attention, and pride that have gone into preserving this remarkable home, making it much more than just a place to stay. It is an experience in itself. Important to mention that Bethel Woods Museum is close by. For anyone who appreciates historic homes, timeless décor, and antique furnishings, this is an absolute must-visit destination. The character and atmosphere of the manor create a sense of stepping back in time while still enjoying every comfort. What made our stay even more memorable was the wonderful owner, America. She was incredibly accommodating, warm, and genuinely hospitable. We enjoyed several great conversations, and her kindness and attention to detail made us feel completely at home. Her passion for the property shines through in every aspect of the guest experience. Kenoza Lake View Manor offers a rare combination of beauty, history, comfort, and heartfelt hospitality. We highly recommend it and would gladly return."

Postcard Cabins Western Catskills, Outdoor Collection by Marriott Bonvoy

8/10 Good

"We had a really nice stay at Postcard Cabins in Roscoe, Western Catskills, NY. The cabin itself was wonderful! Everything was clean, cozy, and thoughtfully provided. We had everything we needed to enjoy our stay, and the overall atmosphere was exactly what we were looking for. However, there was one major disappointment worth mentioning for future guests. We specifically booked the Signature Cabin, which was the highest and most expensive accommodation level offered, because we expected a little more in terms of comfort, privacy, and convenience. Unfortunately, that wasn’t entirely our experience. While we noticed that several of the other cabins had parking directly next to them, our Signature Cabin required us to park elsewhere and walk up a significant number of very steep steps to reach it, carrying all of our belongings. This was something we were never made aware of during the booking process through Expedia. Climbing that many steep steps was physically challenging. I actually had to stop along the way to catch my breath. Had we known about the parking situation and the number of stairs beforehand, we likely would have chosen a different cabin. My biggest suggestion to management would be to clearly disclose these details during the booking process, especially for guests booking through third-party websites. A little transparency goes a long way and allows guests to choose accommodations that best suit their needs."

Find out more about Town of Rockland

Everything you need to know about Town of Rockland 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 Town of Rockland 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 Town of Rockland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Town of Rockland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Rockland. 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 Town of Rockland 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 Town of Rockland vacation rentals we have selected for you start as low as CA $227 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Town of Rockland rentals

At Expedia, we put the best Town of Rockland 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 Town of Rockland 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 Town of Rockland 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 Town of Rockland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Our top choices for Town of Rockland vacation rentals

1. Charming 1 bedroom apartment with AC in quaint Roscoe

2. Catskills Adventures

3. Tiny Home * Big Mountain View’s * Cozy Fireplace

4. The Roscoe Rise - Hot Tub Sauna Fire Pit MCM Cabin

5. Waterfront property, perfect winter getaway, directly on the Willowemoc!

6. Hot Tub, Private Dock, Quiet Lake Home

7. Welcome Families and Friends to the Home of Laughter and More Laughter

8. CABIN TENT ON WORKING RANCH NEAR BETHEL WOODS

9. Postcard Cabins Western Catskills, Outdoor Collection by Marriott Bonvoy

10. Suites on Main

11. Starlite Motel

12. Charming Swan Lake Retreat w/ Hot Tub & Deck

13. Turey Forest Camping Near Bethel Woods - 15 minutes to Bethel Woods, Casino,

14. Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

15. Off-Grid Tiny Cabin with Cozy Vintage Charm

16. Roscoe Cottage Pet Friendly

17. Lakeview Cabin Duplex

18. New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi

19. Handcrafted Riverfront Cabin on 10 acres

20. Callicoon Creek Farmhouse

Find vacation rentals that suit your style

Top Town of Rockland Hotel Reviews

Hampton Inn Monticello

Kenoza Lake View Manor

Shandaken Inn

Postcard Cabins Western Catskills, Outdoor Collection by Marriott Bonvoy

Super 8 by Wyndham Monticello NY

The Alder at Resorts World Catskills

Urban Cowboy Lodge

Find out more about Town of Rockland