Top Town of Olive Hotels: 2026 Best Hotels in Town of Olive

Top Cities in Town of Olive

A large lake with a bridge, surrounded by mountains and greenery.

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Town of Olive hotels

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

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

Shokan

MIKE W.

$178 nightly

Oct 18 - Oct 19

Total with taxes and fees

A conservatory with wicker furniture, a glass coffee table, and a view of the outdoors.

2. High Point Mtn House ~ Celebrate Summer ~ Privacy ~ SERENITY NOW~ Gorgeous VIEWS

Olivebridge

hannah c.

A spacious living room with a high ceiling, a fireplace, a television, and a large window overlooking a deck.

3. Relaxing Catskill Mountain Cottage.

West Shokan

Emily C.

A living room with a sofa, television, and plants.

4. Mid-Century Ranch * One-Level Living * Quiet Garden

Olivebridge

$594 nightly

Nov 2 - Nov 3

Total with taxes and fees

A living room with a sofa, a coffee table with magazines, and a floor lamp.

5. Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Olivebridge

Tanya R.

A spacious living area with a high ceiling, a staircase, and a kitchen in the background.

6. NEW LISTING! Modern Luxury Catskills Retreat

Olivebridge

Melissa V.

A spacious kitchen with a large island, wooden beams, pendant lights, and a view of the outdoors.

7. Catskills Family Hideaway

Olivebridge

Sarah H.

A deck with chairs overlooking a valley and mountains.

8. Stylish Mountain House with Reservoir Views, Near Woodstock NY

Shokan

"The home was lovely and the view was absolutely stunning. You get this view from all but 1 room. I rated at mid point because the primary rooms bathroom has 0 curtains. Which for the first day seemed fine, until I could see our neighbors walking about. After that we concluded that, yes they can see into the very back of the bathroom, even the toilet. I was very disenchanted at that point. As for the hot tub, the water never got beyond tepid and had issues that needed calls and effort to get back...

Joney B.

A kitchen with a large island, wooden beams, white cabinetry, and bar stools.

9. Charming 2-bedroom cottage on private 4 acres with modern amenities

Olivebridge

A spacious living area with a high ceiling, wooden beams, and large windows. There are multiple seating arrangements including a sofa, chairs, and a dining table.

10. AutoCamp Catskills

Saugerties

Raquel

$179 nightly

Nov 3 - Nov 4

Total with taxes and fees

A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

11. Hunter Lodge, a Bluebird by Lark

Hunter

Marina

$147 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

12. Emerson Resort & Spa

Mount Tremper

Ashley

$163 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

13. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

Ryan

$197 nightly

Nov 12 - Nov 13

Total with taxes and fees

A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.

14. The Graham & Co.

Phoenicia

$156 nightly

Nov 2 - Nov 3

Total with taxes and fees

A historic white building with a porch, American flags, and a sign for Beekman Arms Inn.

15. Beekman Arms and Delamater Inn

Rhinebeck Village

$169 nightly

Nov 9 - Nov 10

Total with taxes and fees

A wooden cabin with a circular window overlooking a lake and grassy area.

16. Hutton Brickyards Riverfront Hotel + Venue

Kingston

Victoria

$312 nightly

Oct 26 - Oct 27

Total with taxes and fees

A large, multi-story hotel with a symmetrical facade, multiple balconies with flower boxes, and a central entrance with a fountain.

17. Mirbeau Inn & Spa

Rhinebeck Village

Maria

$489 nightly

Nov 9 - Nov 10

Total with taxes and fees

A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

18. Hotel Mountain Brook

Tannersville

Kristen

$234 nightly

Nov 8 - Nov 9

Total with taxes and fees

An outdoor patio with a fire pit, seating, and a building in the background.

19. Courtyard by Marriott Kingston

Kingston

Ana

$127 nightly

Oct 25 - Oct 26

Total with taxes and fees

A bathroom with a walk-in shower, grab bars, a toilet, and a small sink.

20. Kingston Regency Inn

Kingston

Stephen

$138 nightly

Nov 2 - Nov 3

Total with taxes and fees

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Town of Olive Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent

"Everything we needed for our stay, clean room and friendly staff, easy to park was a plus!! Idk how hotels are ranked but this is definitely better than a 2star in my opinion. I have been all over the place staying in hotels and this was a great experience!! Especially if all you need is a place to clean up and lay your head, that’s all we usually use hotels for because we are always on the go doing activities when needing a hotel!"

Super 8 by Wyndham Kingston

8/10 Good

"Josh was super helpful at Check-in. Very accommodating and super polite. The property was heavily used by semi-permanent guests and needed a bit of cleaning. I was there to close out a storage unit, so the accommodation was very adequate with close proximity to good eateries and downtown Kingston. My room was quiet and had everything I needed. All good."

Emerson Resort & Spa

8/10 Good

"This is a wonderful place to stay. I love the rustic lodge. We stayed in the Bear. The beds were fabulous and the room is spacious. The bathroom needs to be redone. The toilet is low and the vanity is dated. There should be a lighted mirror and extra lighting in the bathroom. Otherwise, the Emerson meets my expectations!"

AutoCamp Catskills

8/10 Good

"Our stay was great , we really enjoyed the clubhouse the boardgames, a small hike on the property and the airstream was nicely equipped with outside grill, smart tv, and very nice outdoor space. Cleaning wise it was okay, we found hair in the shower drain, futon cover felt unwashed and I wish they had coffee in the clubhouse throughout the day. Would definitely recommend it!"

Mirbeau Inn & Spa

10/10 Excellent

"We had an exceptional stay here! The room was huge, clean, and the amenities top notch! Staff were friendly, engaging, and they could not have been more welcoming! Our spa experiences were more than wonderful, and the spa itself is one to experience for sure! An evening at the bar for dinner was heightened by exceptional service provided by Bella! We undoubtedly look forward to returning soon!"

Search Hotels in Town of Olive

Upfront pricing

Treat yourself

Be picky

Top Cities in Town of Olive

Olivebridge

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Town of Olive hotels

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

2. High Point Mtn House ~ Celebrate Summer ~ Privacy ~ SERENITY NOW~ Gorgeous VIEWS

3. Relaxing Catskill Mountain Cottage.

4. Mid-Century Ranch * One-Level Living * Quiet Garden

5. Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

6. NEW LISTING! Modern Luxury Catskills Retreat

7. Catskills Family Hideaway

8. Stylish Mountain House with Reservoir Views, Near Woodstock NY

9. Charming 2-bedroom cottage on private 4 acres with modern amenities

10. AutoCamp Catskills

11. Hunter Lodge, a Bluebird by Lark

12. Emerson Resort & Spa

13. Kaatskill Mountain Club & Condos by Vail Resorts

14. The Graham & Co.

15. Beekman Arms and Delamater Inn

16. Hutton Brickyards Riverfront Hotel + Venue

17. Mirbeau Inn & Spa

18. Hotel Mountain Brook

19. Courtyard by Marriott Kingston

20. Kingston Regency Inn

Top Town of Olive Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Explore a world of travel with Expedia

Go further with the Expedia app