A mountainous landscape with a clear sky and scattered clouds.

Oliverea Vacation Rentals

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November 2026

December 2026

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Our top choices for Oliverea vacation rentals

A spacious living room with a wooden floor, a flat-screen TV, a wooden table with benches, and large sliding glass doors leading to an outdoor deck.

1. Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

Big Indian

Richard

$700 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

2. Starlite Motel

Big Indian

Stephen

$145 nightly

Nov 11 - Nov 12

Total with taxes and fees

3. 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

$128 nightly

Nov 11 - Nov 12

Total with taxes and fees

A spacious living area with a sofa, a coffee table, and a view of the outdoors.

4. Serene Private Mountain Retreat, Hot Tub for 6, Firepit, Stunning Views and more

Arkville

Daniel P.

$427 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

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

Shandaken

afsoon p.

$160 nightly

Nov 30 - Dec 1

Total with taxes and fees

A living room with a television, two sofas, a patterned rug, and a chandelier.

6. Fantastic 3-bedroom house right near Belleayre mountain ski center in Highmount

Pine Hill

carolyn h.

$440 nightly

Nov 11 - Nov 12

Total with taxes and fees

A two-story house with a dark exterior, a front porch, and a well-maintained lawn.

7. Purple Victorian Vacation Home near Belleayre

Pine Hill

Keith V.

$563 nightly

Nov 12 - Nov 13

Total with taxes and fees

A room with a wooden cabinet, a glass door leading to a closet, a blue patterned rug, and a wooden floor.

8. 1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

Phoenicia

joan b.

$301 nightly

Nov 30 - Dec 1

Total with taxes and fees

A cozy wooden cabin room with a bed, ottomans, a TV, and a large window offering a view of the outdoors.

9. Catskills Tiny Cabin + Private Sauna & Cold Splash, Near Belleayre

Arkville

Tony L.

$356 nightly

Nov 11 - Nov 12

Total with taxes and fees

A bedroom with a large window, wooden ceiling, and a bed with white bedding and two decorative pillows.

10. PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

Mt. Tremper

cheryll s.

A two-story building with large windows and a storefront.

11. Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Windham

Rebecca

$110 nightly

Nov 11 - Nov 12

Total with taxes and fees

A natural setting with a stream, red chairs, and a forested area.

12. Streamside Cottage Half Mile to Town of Woodstock

Woodstock

Anonymous traveler

$267 nightly

Nov 11 - Nov 12

Total with taxes and fees

A wooden deck with a bench, surrounded by a forested area.

13. West Wing - a unique private space w/patio

Shokan

Ronald

$186 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

14. Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Lanesville

Holly

$741 nightly

Nov 21 - Nov 22

Total with taxes and fees

15. Windham NY Escape

Hensonville

Miguel

$502 nightly

Nov 11 - Nov 12

Total with taxes and fees

A triangular wooden cabin with a glass front, a bench, and a table inside.

16. The Bend: Meadow Suite • Pool • Sauna • Fire Pits

Phoenicia

$416 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern kitchen with a large island, a sink, and wooden stools.

17. Woodstock Historic Artist Estate - The Carriage House

Woodstock

Fran W.

$430 nightly

Nov 11 - Nov 12

Total with taxes and fees

A cozy living room with a leather sofa, a fireplace, and a Netflix sign.

18. Steps to Slopes | Hunter Mountain Ski In and Out

Lanesville

Krista F.

$208 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.

19. Belleayre Grandhouse 6 bedrooms sleep 15 w/hot tub, sauna, game lounge.

Margaretville

John K.

$817 nightly

Nov 11 - Nov 12

Total with taxes and fees

A living room with a leather rug, wooden chairs, a sofa, and a decorative wall hanging.

20. 2BR Barnhouse Horse Farm Views by hiking, Phoenicia, Hunter

Hunter

Evan H.

$276 nightly

Nov 11 - Nov 12

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Top Oliverea Hotel Reviews

A rustic interior with a stone fireplace, wooden beams, and a chandelier.

Urban Cowboy Lodge

Big Indian

10/10 Excellent

Carolena

A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

Shandaken Inn

Shandaken

10/10 Excellent

Anonymous traveler

A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.

Emerson Resort & Spa

Mount Tremper

10/10 Excellent

Karla

A large two-story house with a snow-covered roof and a front porch.

Meadowood Inn

Arkville

10/10 Excellent

John

A dining area with a stone fireplace, wooden beams, and large windows.

Phoenicia Lodge

Phoenicia

10/10 Excellent

Anonymous traveler

A restaurant interior with wooden walls, a bar area, and a ceiling with intricate patterns.

Blue Hill Lodge

Claryville

10/10 Excellent

I knew the moment I drove up that this was a great find. Perfect blend of country charm and convenience. Great little restaurant/deli/general store, with friendly and efficient staff. Restaurant had some great Russian specialty foods and beers. Liquor store on premises too. The room was simple and comfortable with a good tv and its own themostat, and really, really clean! I'm looking forward to coming back in spring 2015 when the microbrewery opens.

Curtis

The Wheelhouse Inn

Pine Hill

10/10 Excellent

We stayed here for 3 nights with our 2 young children for a long ski weekend. The location exceeded our expectations: the hotel is located less than 5 minutes from Belleayre Mountain. For a family with young children, the convenience factor couldn't be beat. The inn is nestled in the quaint town of Pine Hill (there's really only one road). There are a few restaurants on the same road, all within easy strolling distance. While there isn't breakfast on premise, there is a new coffee shop right...

Anonymous traveler

Howland House

Mount Tremper

10/10 Excellent

A very nice experience, the Howland House is a very charming guesthouse with cozy, rooms, an excellent restaurant, Oliver’s, right downstairs and a really welcoming atmosphere. Staff were helpful and friendly, really couldn’t have asked for a nicer stay. We had a standard room with a shared bathroom, but the way it was setup made it totally comfortable. Highly recommended place if you’re in the area and we’ll almost certainly return.

Ira

A multi-story building with outdoor seating and a stone-paved patio.

Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

10/10 Excellent

Joseph

A white house with a green door, black trim, and a porch with a lantern.

Twin Gables of Woodstock

Woodstock

10/10 Excellent

One of the coolest and most accommodating places I have ever stayed. If you are coming to Woodstock are even thinking about it this is the place for you. All the rooms are unique, they are super clean and look exactly like they do online. The owner is amazing and she will point you in the right direction for whatever you are looking to do in town. Seriously cannot recommend enough and can’t wait to come back.

Noah

Find out more about Oliverea

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

Oliverea vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oliverea. 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 Oliverea 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 $118 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 Oliverea rentals

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