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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Cottages in Town of Olive

Exterior
Streamside Cottage Half Mile to Town of Woodstock

Cottage in Woodstock

10.0 out of 10, Exceptional, (259)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
$346 nightly
The price is $388
Dec 13 - Dec 14
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Exterior detail
Charming loft cottage in tranquil Germantown with WiFi, AC

Cottage in Germantown

10.0 out of 10, Exceptional, (4)
"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.
$191 nightly
The price is $214
Nov 30 - Dec 1
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
Exterior
Relaxing Catskill Mountain Cottage.

Cottage in West Shokan

10.0 out of 10, Exceptional, (52)
"Wonderful experience and beautiful property."
United States
James B.
Relaxing Catskill Mountain Cottage.
Exterior
Experience Peace in this Cozy country cottage nestled beneath the mountains

Cottage in Catskill

9.8 out of 10, Exceptional, (8)
"Very comfortable cottage in a lovely area. Grateful for the ac on those very hot days! Loved grilling on the porch and the big patio umbrellas. Host is very responsive and helpful when needed. Hope to come again! "
United States
Laura G.
$309 nightly
The price is $334
Nov 25 - Nov 26
Total with taxes and fees
Experience Peace in this Cozy country cottage nestled beneath the mountains
Interior
Private cottage - 5 min from the center of town

Cottage in Woodstock

10.0 out of 10, Exceptional, (15)
"Stay was fabulous! Host is amazing- welcoming and courteous. We loved the wine and fresh fruit with chocolates!"
United States
Sandra
Private cottage - 5 min from the center of town
Exterior
Woodstock Cottage with hot tub. Close to town yet very private.

Cottage in Woodstock

9.4 out of 10, Exceptional, (86)
"Diana’s property was the perfect spot to reconnect with old friends. We enjoyed the art, food and music of Woodstock and a side trip to Bethel to check out the Woodstock Museum. Diana’s home was a comfortable place to retreat to after our days of exploring. We would love to make it an annual event. "
United States
Barbara H.
Woodstock Cottage with hot tub. Close to town yet very private.
Exterior
Charming 2-bedroom cottage with large deck in beautiful Accord NY.

Cottage in Accord

10.0 out of 10, Exceptional, (16)
"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.

Cottage in Saugerties

10.0 out of 10, Exceptional, (12)
"Great spot!"
United States
Dylan
$159 nightly
The price is $178
Nov 25 - Nov 26
Total with taxes and fees
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

Cottage in Woodstock

10.0 out of 10, Exceptional, (78)
"Small and cozy.. super clean and beautiful place to reset especially if you’re not from the areaWill definitely stay again"
United States
K H.
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Exterior
Little red house just outside of Woodstock

Cottage in Bearsville

9.0 out of 10, Wonderful, (2)
"The house is cute, well decorated but very small "
United States
Harry
$468 nightly
The price is $524
Nov 27 - Nov 28
Total with taxes and fees
Little red house just outside of Woodstock
Terrace/patio
Charming Artist's Retreat

Cottage in Saugerties

10.0 out of 10, Exceptional, (146)
"Had an amazing stay and will definitely be back :) "
United States
Riley C.
Charming Artist's Retreat
Exterior
Private Cozy Home ~ Hot Tub ~ All Yours ~ In town ~ fenced in yard ~Pets welcome

Cottage in Woodstock

9.8 out of 10, Exceptional, (123)
"Very clean and great location. Easy checkin"
United States
Michael D.
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!

Cottage in Phoenicia

9.8 out of 10, Exceptional, (23)
"The Romantic cottage was comfortable and located in the center of town. We were able to walk to nearby restaurants and shops. The cottage does need some repairs inside and out (which is the only reason that I didn't give it 5 stars). "
United States
Nicole
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Exterior
Adorable Cottage w/ Hot Tub, Pond, and Rain Deck

Cottage in Kerhonkson

9.0 out of 10, Wonderful, (8)
"excellent experience, environment was cozy and inviting "
United States
Richard S.
$655 nightly
The price is $731
Dec 1 - Dec 2
Total with taxes and fees
Adorable Cottage w/ Hot Tub, Pond, and Rain Deck
Exterior
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

Cottage in Woodstock

10.0 out of 10, Exceptional, (171)
"Great holiday weekend. Hiked, ate, shopped and enjoyed music at Levon’s. "
United States
Denis M.
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
Property grounds
Charming Rhinebeck Cottage, 5 min. from town, King Bed!

Cottage in Rhinebeck

10.0 out of 10, Exceptional, (2)
"Wonderful couples getaway. Stunning landscape, wildlife, and views."
United States
Michael T.
Charming Rhinebeck Cottage, 5 min. from town, King Bed!
Terrace/patio
Charming Victorian Ski Cottage minutes to Belleayre Mountain

Cottage in Fleischmanns

10.0 out of 10, Exceptional, (5)
"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

Cottage in Stone Ridge

9.8 out of 10, Exceptional, (56)
"If the hosts ask to meet you, say yes!! They are every bit as fascinating as this location and cottage are. The history behind the place, the talented folks who did the restoration , the peacefulness of the place all combine to make it a perfect location for a country getaway. It is well equipped and located near small towns that offer any supplies or groceries you may need. The hosts offer this accommodation with an authenticity and warmth that is rare. From this safe haven, all manner of great...
United States
Trudy H.
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley
House (3 Bedrooms) | Interior
Mountain Views & Brook Access: Home in Arkville!

Cottage in Arkville

3.0 star property
Mountain Views & Brook Access: Home in Arkville!
House (3 Bedrooms) | Interior
Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish

Cottage in Fleischmanns

3.0 star property
10.0 out of 10, Exceptional, (1)
"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

Super 8 by Wyndham Kingston

Super 8 by Wyndham Kingston

10/10 Excellent
"The clean room stood out — everything was tidy and comfortable. The staff stood out. Everyone was friendly and easy to deal with. The room cleanliness and the helpful staff both made the stay great. The amenities were convenient and everything worked smoothly."
Jonathan 1-night trip
Posted 4 days ago
Super 8 by Wyndham Kingston

Find out more about Town of Olive

Town of Olive Cottages information

Number of reviews
911
Accommodation
174 Cottages
Lowest Price
$178
Highest Price
$731

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