Cottages in Town of Olive

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Top Cities in Town of Olive

aerial view of the ashokan reservoir in upstate new york (near woodstock olivebridge) nyc drinking water and catskill mountains (catskills hills background) park road walkway bridge crossing lake pond
CottagesCottages

Olivebridge

Olivebridge

Our top choices for Town of Olive cottages

Property grounds

Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (267 reviews)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
The price is HK$1,555
HK$3,001 total
includes taxes & fees
6 Feb - 7 Feb
Streamside Cottage Half Mile to Town of Woodstock
Interior

Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (9 reviews)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
The price is HK$852
HK$1,671 total
includes taxes & fees
7 Feb - 8 Feb
Charming loft cottage in tranquil Germantown with WiFi, AC
Exterior

Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.
West Shokan
10.0 out of 10, Exceptional, (58 reviews)
"Wonderful experience and beautiful property."
United States
James B.
Relaxing Catskill Mountain Cottage.
Exterior

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
10.0 out of 10, Exceptional, (12 reviews)
"Very comfortable home"
United States
Holly
The price is HK$1,086
HK$2,497 total
includes taxes & fees
12 Feb - 13 Feb
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Interior

Private cottage - 5 min from the center of town

Private cottage - 5 min from the center of town
Woodstock
10.0 out of 10, Exceptional, (15 reviews)
"Place was perfect for my needs and Irene is a gracious and attentive host!"
United States
Jeremiah D.
Private cottage - 5 min from the center of town
Exterior

Woodstock Cottage with hot tub. Close to town yet very private.

Woodstock Cottage with hot tub. Close to town yet very private.
Woodstock
9.4 out of 10, Exceptional, (90 reviews)
"We had a lovely time and the host was super responsive and caring. The property is lovely and cozy. The fireplace was super easy to use, the beds were comfortable, the amenities were plentiful. The home took a little while to warm up but we are almost at the start of winter and there is snow on the ground. Otherwise, great stay!"
United States
Stephen
Woodstock Cottage with hot tub. Close to town yet very private.
Exterior

Charming 2-bedroom cottage with large deck in beautiful Accord NY.

Charming 2-bedroom cottage with large deck in beautiful Accord NY.
Accord
10.0 out of 10, Exceptional, (20 reviews)
"We enjoyed the peaceful location & being in the mountains. "
United States
James S.
Charming 2-bedroom cottage with large deck in beautiful Accord NY.
Exterior

Country Cottage with beautiful views and easy access to Catskills activities.

Country Cottage with beautiful views and easy access to Catskills activities.
Saugerties
10.0 out of 10, Exceptional, (15 reviews)
"Great spot!"
United States
Dylan
The price is HK$872
HK$1,501 total
includes taxes & fees
6 Feb - 7 Feb
Country Cottage with beautiful views and easy access to Catskills activities.
Exterior

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Woodstock
10.0 out of 10, Exceptional, (79 reviews)
"We had a great stay at the Junebug Cottage. It was a great location, and our hosts were amazing."
United States
Anonymous traveller
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Exterior

Little red house just outside of Woodstock

Little red house just outside of Woodstock
Bearsville
9.0 out of 10, Wonderful, (2 reviews)
"The house is cute, well decorated but very small "
United States
Harry
The price is HK$2,285
HK$4,397 total
includes taxes & fees
9 Feb - 10 Feb
Little red house just outside of Woodstock
Exterior

Charming Artist's Retreat

Charming Artist's Retreat
Saugerties
10.0 out of 10, Exceptional, (147 reviews)
"Very close to everything we needed. Stunning views from the lookout. Gorgeous sunsets. The shower is amazing."
United States
Jean L.
Charming Artist's Retreat
Exterior

Private Cozy Home ~ Hot Tub ~ All Yours ~ In town ~ fenced in yard ~Pets welcome

Private Cozy Home ~ Hot Tub ~ All Yours ~ In town ~ fenced in yard ~Pets welcome
Woodstock
9.8 out of 10, Exceptional, (128 reviews)
"Stayed here for my honeymoon and it was perfect! Private and relaxing, cozy spots to hang out, well stocked kitchen, lovely hot tub, and awesome location right in the middle of town. It was great to get to walk to all the restaurants & shops. The host was responsive and went out of his way to make sure the hot tub was in good working order for our stay which we really appreciated. Check in / check out was incredibly easy. We would definitely stay here again! "
United States
Kirstan B.
Private Cozy Home ~ Hot Tub ~ All Yours ~ In town ~ fenced in yard ~Pets welcome
Exterior

Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!

Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Phoenicia
9.8 out of 10, Exceptional, (23 reviews)
"Cute cottage, very comfy - we enjoyed ourselves a lot!"
United States
Heather G.
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Outdoor spa tub

Secluded Couples Spa Sanctuary with HotTub!

Secluded Couples Spa Sanctuary with HotTub!
Kerhonkson
9.2 out of 10, Wonderful, (9 reviews)
"The Host was very communicative & showed great hospitality. The cottage was cozy & had all we needed. Great secluded quiet area to relax & close to restaurant/coffee shop. "
United States
Beth G.
Secluded Couples Spa Sanctuary with HotTub!
Exterior

TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
Woodstock
10.0 out of 10, Exceptional, (177 reviews)
"Very clean, well appointed, great location and definitely cozy and romantic "
United States
Amen
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
Exterior

Charming Rhinebeck Cottage, 5 min. from town, King Bed!

Charming Rhinebeck Cottage, 5 min. from town, King Bed!
Rhinebeck Village
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful hosts and a spectacular view out the windows!"
United States
David R.
Charming Rhinebeck Cottage, 5 min. from town, King Bed!
Exterior

Charming Victorian Ski Cottage minutes to Belleayre Mountain

Charming Victorian Ski Cottage minutes to Belleayre Mountain
Fleischmanns
10.0 out of 10, Exceptional, (7 reviews)
"Great for wedding up the road at Spillans "
United States
Monica M.
Charming Victorian Ski Cottage minutes to Belleayre Mountain
Exterior

A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley

A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley
Stone Ridge
9.8 out of 10, Exceptional, (57 reviews)
"Beautiful farm property. Visited in the fall and the leaves in the area were stunning. Deer outside window. Hosts were communicative and lovely."
United States
Catherine M.
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley
Interior

Mountain Views & Brook Access: Home in Arkville!

Mountain Views & Brook Access: Home in Arkville!
3.0 star property
Arkville
Mountain Views & Brook Access: Home in Arkville!
Interior

Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish

Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish
3.0 star property
Fleischmanns
10.0 out of 10, Exceptional, (1 review)
"We had a great time during our stay. The house was nicely setup. We would go back again."
United States
Christopher J
Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Town of Olive Hotel Reviews

Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

10/10 Excellent
"We had such a lovely stay! Our room was cozy and warm, and the staff were super friendly and welcoming. We especially enjoyed the little surprise continental breakfast with tea, coffee, and snacks by the fireplace—it made our mornings so nice. The jacuzzi and pool were amazing, and we had a great time relaxing. Dinner at the restaurant was delicious, and our server, Kinga, was wonderful! Everything about our stay was perfect. The only tiny thing was that the bathroom didn’t have hair conditioner (shampoo and body wash were provided), but it really didn’t bother us. We would definitely come back—highly recommend! 😊"
Olena 1-night trip
Posted 23 hours ago
Kaatskill Mountain Club at Hunter Mountain

Find out more about Town of Olive

Town of Olive Cottages information

Number of reviews
962
Accommodation
173 Cottages
Lowest Price
HK$1,501
Highest Price
HK$4,397

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