Top Guest Houses in Town of Olive in 2026

A mountainous landscape with autumn foliage.

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Our top choices for Town of Olive guest houses

A blue door with a white frame, a small table with a chair, a rug, and potted plants on the porch.

1. The Wiltwyck

Kingston

ALEJANDRO

Rp6.347.794 total

includes taxes & fees

18 Oct - 19 Oct

A living room with a stone fireplace, blue sofas, a wooden coffee table, and a ceiling fan.

2. Moondance Ridge Bed & Breakfast

New Paltz

Anthony

Rp5.631.319 total

includes taxes & fees

1 Nov - 2 Nov

A large, white, two-story house with a turret and a wrap-around porch, surrounded by lush greenery.

3. Shadowcrest

Fleischmanns

David

Rp2.598.933 total

includes taxes & fees

15 Oct - 16 Oct

A hallway with a door marked with the number 3, leading to a room with a white door and a brass doorknob.

4. The Woodbine Inn

Palenville

Allyson

A modern house with a wooden deck, a fire pit, and a covered outdoor seating area.

5. The Herwood Inn

Woodstock

Diana

Rp5.252.378 total

includes taxes & fees

22 Oct - 23 Oct

A house with a porch, a garden with ferns and flowering plants, and a red flowering tree.

6. The Gables of Rhinebeck Inn

Rhinebeck Village

maryeliza

Rp5.262.759 total

includes taxes & fees

2 Nov - 3 Nov

A long, narrow hallway with wooden beams and a polished floor, leading to a door at the end.

7. The Old Catskill Game Farm Inn

Catskill

Gustavo

A wooden deck with a railing, potted plants, and a view of a green landscape.

8. The 1850 House Inn and Tavern

Rosendale

Seth

A historic building with a large arched window and ivy-covered walls, surrounded by outdoor seating and lanterns.

9. Church Des Artistes Guest House

Rondout

"This was a very overpriced bed and breakfast! The owners were quite pleasant, but there were several things about this establishment that raised a flag. For one, we had to go down the hall and down a full flight of stairs to the bathroom. At the bottom of the stairs (where our "private bathroom" was) was also the door to the entrance of the house. Althugh there was not much traffic, it was still rather uncomfortable to walk up the stairs with my towel on! Our beds were never made on...

Carole

10. Bohemian Inn

Saugerties

"My husband summed up our overnight stay. He said, "I feel like we just had a mini vacation!" The Bohemian Inn is in such a convenient location. You can walk to to most anything you might want/need. Stephanie, the owner/operator of the Inn was wonderful! She made our stay feel as though we were visiting an old friend, while maintaining privacy. The rooms are lovely. They are beautifully and uniquely decorated. And spotlessly clean!! A mini, wonderful vacation, indeed! Working in...

Tiffany L.

11. Gateway Lodge Bed & Breakfast

Highmount

Aaron

A large, two-story house with a steeply pitched roof, surrounded by dense forest.

12. Spillian

Arkville

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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!"

Find out more about Town of Olive

Town of Olive Guest Houses information

Number of reviews	788
Accommodation	12 Guest Houses
Lowest Price	Rp2.598.933
Highest Price	Rp6.347.794

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Town of Olive guest houses

1. The Wiltwyck

2. Moondance Ridge Bed & Breakfast

3. Shadowcrest

4. The Woodbine Inn

5. The Herwood Inn

6. The Gables of Rhinebeck Inn

7. The Old Catskill Game Farm Inn

8. The 1850 House Inn and Tavern

9. Church Des Artistes Guest House

10. Bohemian Inn

11. Gateway Lodge Bed & Breakfast

12. Spillian

Top Town of Olive Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Kaatskill Mountain Club & Condos by Vail Resorts

Super 8 by Wyndham Kingston

Beekman Arms and Delamater Inn

Quality Inn Hyde Park Poughkeepsie North

Kingston Regency Inn

Emerson Resort & Spa

AutoCamp Catskills

Mirbeau Inn & Spa

Find out more about Town of Olive

Town of Olive Guest Houses information

Explore a world of travel with Expedia