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

1. Moondance Ridge Bed & Breakfast

New Paltz

Anthony

Rp4.483.007 total

includes taxes & fees

27 Aug - 28 Aug

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

2. The Herwood Inn

Woodstock

John

Rp4.148.133 total

includes taxes & fees

16 Sept - 17 Sept

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

3. The Wiltwyck

Kingston

Terry

Rp3.296.672 total

includes taxes & fees

27 Aug - 28 Aug

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

4. Shadowcrest

Fleischmanns

Alyson

Rp2.573.089 total

includes taxes & fees

1 Sept - 2 Sept

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

5. The Gables of Rhinebeck Inn

Rhinebeck Village

maryeliza

Rp4.546.740 total

includes taxes & fees

27 Aug - 28 Aug

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

6. The Woodbine Inn

Palenville

Allyson

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

Howard

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

8. The 1850 House Inn and Tavern

Rosendale

Seth

9. 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.

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

10. 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

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

"Convenient location, breakfast a plus, clean rooms. Unfortunately the WiFi was not working, but it was being fixed while we were there"

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent

"Everything was great...fun bar, very nice rooms with kitchen small living room area. But the reason we stayed was the Culinary Institute. The staff told us it was a 5 min walk, Please be advised it is not 5 min more like 10-15 min. The hill from the hotel is step and it's also steep to go up to the Culinary Institute. If your young its fine. But people who don't walk to well should expect to take and Uber maybe 7-10.00$ We took and Uber home because it was dark out after we had our dinner. You can pick up and Uber very easy by the students dorms."

Residence Inn by Marriott Kingston

10/10 Excellent

"We liked that the room was spacious and clean. We were able to check in early. The only thing we didn’t like is that there were pets in the hotel - we learned when our neighbor’s dog was barking. We hope there was never a dog in our room as we are allergic. We don’t know how that works."

Find out more about Town of Olive

Town of Olive Guest Houses information

Number of reviews	928
Accommodation	13 Guest Houses
Lowest Price	Rp2.573.089
Highest Price	Rp4.546.740

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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. Moondance Ridge Bed & Breakfast

2. The Herwood Inn

3. The Wiltwyck

4. Shadowcrest

5. The Gables of Rhinebeck Inn

6. The Woodbine Inn

7. The Old Catskill Game Farm Inn

8. The 1850 House Inn and Tavern

9. Bohemian Inn

10. Church Des Artistes Guest House

11. Gateway Lodge Bed & Breakfast

12. Spillian

Top Town of Olive Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Courtyard by Marriott Kingston

Beekman Arms and Delamater Inn

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Americas Best Value Inn New Paltz

AutoCamp Catskills

Residence Inn by Marriott Kingston

Howard Johnson by Wyndham Saugerties

Hunter Lodge, a Bluebird by Lark

Find out more about Town of Olive

Town of Olive Guest Houses information

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