Olivebridge Vacation Home Rentals from CA $213: Search Top Private Vacation Homes for Rent

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

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Our top choices for Olivebridge vacation homes

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

A spacious living room with a television, large windows, and a ceiling fan.

A house with a green roof, a deck, and a lawn.

A dining area with a wooden table, black upholstered chairs, a wooden cabinet with records, and a potted plant.

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

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

Olivebridge

The price is CA $186

CA $186

CA $796 total

includes taxes & fees

Oct 27 - Oct 28

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

A modern two-story house with a deck, a swimming pool, and outdoor seating.

A modern kitchen with a central island, pendant lights, and large windows offering a view of trees.

A modern two-story house with a steeply pitched roof, surrounded by lush greenery and a well-maintained garden.

A modern kitchen with a large island, stainless steel appliances, and a view of trees through large windows.

2. Hot Tub * Fireplace * Close To Woodstock

Hot Tub * Fireplace * Close To Woodstock

West Hurley

9.6 out of 10, Exceptional, (4 reviews)

9.6/10

Exceptional

(4 reviews)

"Beautiful place! "

Cheryl U.

The price is CA $462

CA $462

CA $1,338 total

includes taxes & fees

Oct 25 - Oct 26

Hot Tub * Fireplace * Close To Woodstock

A kitchen with grey cabinets, a stone floor, and a view of a garden through an open door.

A rustic dining area with a wooden table and chairs, a stone fireplace, and a view of the outdoors.

A modern kitchen with grey cabinets, a stone floor, and a skylight.

A rustic room with a fireplace, wooden beams, a bookshelf, and a wicker chair.

3. Historic Cottage * Steam Shower * Chef’s Kitchen

Historic Cottage * Steam Shower * Chef’s Kitchen

Kingston

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"We had a great time staying here! The house is a gorgeous historic house with modern amenities. It was a short drive to Kingston which was super convenient. We loved that we could bring our dog with us as well. It is on a main road, but we didn't find that to be a disturbance at all. I would definitely come back here again!!"

Laura D.

The price is CA $220

CA $220

CA $711 total

includes taxes & fees

Nov 18 - Nov 19

Historic Cottage * Steam Shower * Chef’s Kitchen

A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

A bathroom with a wooden vanity, a round mirror, a wall-mounted light fixture, and a towel on the counter.

A two-story house with a porch and a staircase leading to the upper level.

A rustic wooden cabin with a chimney, a door, and a small porch area.

4. Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

Stone Ridge

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."

Tarun

The price is CA $183

CA $183

CA $365 total

includes taxes & fees

Nov 1 - Nov 2

Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

A modern bedroom with a large bed, bedside tables, a chair, and a view of the outdoors through a glass door.

A dining table with a marble top, surrounded by wicker chairs, under a white pendant light.

A bathroom with a marble sink, a framed painting, a window with a blind, and a small wooden side table with a lamp.

A modern kitchen with a dining area, featuring a central island, black cabinets, and a built-in oven.

5. Stone Ridge Modern Mountain House

Stone Ridge Modern Mountain House

Stone Ridge

9.6 out of 10, Exceptional, (4 reviews)

9.6/10

Exceptional

(4 reviews)

"We enjoyed our one night stay. House was very clean and well appointed. Host was responsive. "

Margaret and Greg S.

The price is CA $436

CA $436

CA $897 total

includes taxes & fees

Nov 3 - Nov 4

Stone Ridge Modern Mountain House

A bedroom with a bed, a TV mounted on the wall, a window with a view of greenery, and a small seating area with a table and chairs.

A bathroom with a white sink, a mirror, and a window.

A wooden cabin with a metal roof, surrounded by a grassy yard with a fire pit and red Adirondack chairs.

A wooden cabin with a red roof, surrounded by lush greenery and orange flowers.

6. The Studio at the Inn at High Falls

The Studio at the Inn at High Falls

High Falls

8.0 out of 10, Very good, (46 reviews)

8.0/10

Very good

(46 reviews)

"Great property in a serene setting. We enjoyed it very much!"

John M.

The price is CA $158

CA $158

CA $376 total

includes taxes & fees

Oct 25 - Oct 26

The Studio at the Inn at High Falls

A house with a sloped roof, a front porch with two chairs, and a well-maintained lawn.

A compact kitchen with wooden cabinets, a microwave, a sink, and a dining area with chairs and a table.

A spacious loft with high ceilings, a large skylight, a cozy seating area with a sofa and armchairs, and a wooden coffee table.

A room with a wooden floor, a sofa, a table, a lamp, a radiator, and a window with curtains.

7. Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!

Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!

Woodstock

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"Great location."

Louis

The price is CA $280

CA $280

CA $474 total

includes taxes & fees

Oct 26 - Oct 27

Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!

A staircase with wooden steps and a black handrail, leading to a white door.

A bedroom with a bed, a grey sofa, a wooden wardrobe, and two abstract paintings on the wall.

A spacious living room with a grey sofa, a patterned rug, and large windows offering a view of trees.

A swimming pool with a curved edge, surrounded by lush greenery and a house with a deck.

8. NEW: Family Retreat * Fireplace * Spa Bathroom

NEW: Family Retreat * Fireplace * Spa Bathroom

Cottekill

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Property was great for our girls weekend! Eight of us fit very comfortably. Host was very responsive to all of our needs! We had a great time!"

Shannon M.

The price is CA $231

CA $231

CA $1,173 total

includes taxes & fees

Oct 27 - Oct 28

NEW: Family Retreat * Fireplace * Spa Bathroom

A spacious living room with a fireplace, comfortable seating, and a dining area with a wooden table.

A modern kitchen with a large island, bar stools, and a view of the outdoors through large windows.

A modern living room with a large sofa set, a coffee table, and a chandelier.

A wooden console table with a book and a sculpture, a framed picture of a horse, and a potted plant.

9. LONGVIEW FARM - Reimagined Modern Farmhouse

LONGVIEW FARM - Reimagined Modern Farmhouse

Marbletown

The price is CA $1,302

CA $1,302

CA $2,729 total

includes taxes & fees

Nov 18 - Nov 19

LONGVIEW FARM - Reimagined Modern Farmhouse

A spacious living area with a wooden dining table, a sofa with cushions, and a staircase leading to an upper level.

A modern living room with a fireplace, a large sofa, a dining area, and a kitchen with a refrigerator and microwave.

A wooden hot tub surrounded by snow-covered trees, with a wooden deck and railing.

A modern kitchen with a central island, wooden cabinets, and a large window.

10. Hot Tub * Stylish Family Home * 2nd Guest Suite

Hot Tub * Stylish Family Home * 2nd Guest Suite

Stone Ridge

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Beautiful home, well appointed, hot tub was great, pet friendly, and incredible communication with the hosts! "

Rebecca K.

The price is CA $340

CA $340

CA $1,316 total

includes taxes & fees

Oct 29 - Oct 30

Hot Tub * Stylish Family Home * 2nd Guest Suite

A modern living room with a large window, a dining area with a round table, and a cozy seating area with a fur throw.

A modern kitchen with a large island, a sink, and wooden stools.

A wooden dining table with a potted plant, a pendant light, and a wall-mounted clock.

A bedroom with a large bed, two nightstands, a window, and a plain wall.

11. Woodstock Historic Artist Estate - The Carriage House

Woodstock Historic Artist Estate - The Carriage House

Woodstock

9.8 out of 10, Exceptional, (50 reviews)

9.8/10

Exceptional

(50 reviews)

"We had a wonderful time, again! Perfect location!"

Fran W.

The price is CA $211

CA $211

CA $627 total

includes taxes & fees

Oct 26 - Oct 27

Woodstock Historic Artist Estate - The Carriage House

A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

A bedroom with a bed, a TV on a white dresser, a window with blinds, and a ceiling light fixture.

A compact kitchen with a stainless steel refrigerator, a bar stool, and a dining area with a red rug.

12. Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Kingston

9.6 out of 10, Exceptional, (108 reviews)

9.6/10

Exceptional

(108 reviews)

"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"

Nan

The price is CA $220

CA $220

CA $351 total

includes taxes & fees

Nov 9 - Nov 10

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

A bedroom with a bed, a chair with a yellow cushion, a potted plant, and a window with curtains.

A modern kitchen with white cabinets, a built-in oven, and a dining area with a black rug and metal chairs.

A kitchen with a dining area, wooden flooring, a ceiling fan, and a window with blinds.

13. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!

Kingston

10.0 out of 10, Exceptional, (33 reviews)

10/10

Exceptional

(33 reviews)

"Great multi-week stay! Would certainly stay again. "

Jim R.

The price is CA $105

CA $105

CA $355 total

includes taxes & fees

Nov 3 - Nov 4

Campfire Cottage: Fireplace, fire pit & no chores!

A compact kitchen with blue cabinets, a white stove, and yellow chairs.

A living room with a sofa, armchair, coffee table, and a TV.

A modern living room with a wooden floor, a blue chair, a yellow chair, a sofa, and a desk with a computer.

A living room with a sofa, armchair, and coffee table, a TV on a wooden stand, and a window with a floor lamp.

14. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Kingston

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"

Brendan B.

The price is CA $97

CA $97

CA $345 total

includes taxes & fees

Oct 27 - Oct 28

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

A tent with a central pole, a view of the forest through the entrance, and a bed with patterned bedding.

A wooden sign for Minnewaska State Park Preserve with a stone base.

A forest campsite with a tent, a fire pit, and a bench.

A waterfall cascading into a calm pool surrounded by rocky cliffs and dense greenery.

15. Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park

Kerhonkson

9.0 out of 10, Wonderful, (4 reviews)

9.0/10

Wonderful

(4 reviews)

"This place was amazing and our hosts were as equally as awesome as their campsite. My family highly recommends this place! It's got everything you need and is close to so many beautiful hiking and swimming areas!"

Andie C.

The price is CA $120

CA $120

CA $213 total

includes taxes & fees

Oct 25 - Oct 26

Glamping Tent & Campsite by Minnewaska State Park

A spacious living room with a large window, a modern sofa, a coffee table, and a bookshelf.

A modern kitchen with a central island, black cabinetry, and pendant lighting.

A modern house with a glass facade, a stone pathway, and a pond.

A chandelier with multiple glass wine glasses hanging from a wooden beam.

16. Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House

Woodstock

9.8 out of 10, Exceptional, (14 reviews)

9.8/10

Exceptional

(14 reviews)

"We had a short stay but absolutely loved the house. Perfect location, lots of space, and the hosts were great. Would stay again, highly recommend!"

Strati P.

The price is CA $426

CA $426

CA $893 total

includes taxes & fees

Oct 25 - Oct 26

Woodstock Historic Artist Estate - The Museum House

A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

A living room with a TV on a wooden stand, a colorful wall mural, a large plant, and a cozy seating area with cushions.

A compact kitchen with a white refrigerator, a stove, and a microwave. There are yellow chairs around a small table, and blue cabinets above the counter.

17. Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!

Kingston

9.6 out of 10, Exceptional, (15 reviews)

9.6/10

Exceptional

(15 reviews)

"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "

Kelley Marie

The price is CA $127

CA $127

CA $427 total

includes taxes & fees

Nov 2 - Nov 3

Retro Retreat: renovated 2BR, desk, no chore list!

A spacious living area with a high ceiling, wooden beams, two leather sofas, a central rug, and a staircase leading to an upper level.

A cozy living room with two leather sofas, a wooden dining table, and large windows offering a view of the outdoors.

A cozy attic bedroom with a wooden ceiling, a large window, a bed with a striped blanket, a bedside table with a lamp, and a cabinet.

A kitchen with wooden cabinets, a microwave, and a sink. There is a sliding glass door leading to an outdoor area with a wooden deck.

18. The Loft At The Inn At High Falls

The Loft At The Inn At High Falls

High Falls

8.8 out of 10, Excellent, (24 reviews)

8.8/10

Excellent

(24 reviews)

"this was just a lovely stay all around!! Will absolutely stay there again!"

Inez

The price is CA $252

CA $252

CA $496 total

includes taxes & fees

Oct 25 - Oct 26

The Loft At The Inn At High Falls

A kitchen with wooden shelves, a window with a view of trees, and a vase with flowers on the windowsill.

A kitchen with wooden ceiling, white cabinets, a dining table with chairs, and a refrigerator.

A cabin with a wooden deck, a porch, and a small garden area.

A bedroom with a large bed, a fireplace, and two windows with curtains.

19. Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Kerhonkson

10.0 out of 10, Exceptional, (47 reviews)

10/10

Exceptional

(47 reviews)

"Sweet place, very close to Minnewaska State Park which was great for us"

Sueane

The price is CA $160

CA $160

CA $290 total

includes taxes & fees

Nov 1 - Nov 2

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

A stone pathway leading to a white gate, surrounded by lush greenery and a red building.

A cozy living room with a wood-burning stove, leather furniture, and a view of the outdoors.

A covered outdoor seating area with wicker furniture, a blue rug, and a view of a wooden deck and trees.

A modern kitchen with white cabinets, a black countertop, and a window with a view of greenery.

20. Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.

Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.

Accord

10.0 out of 10, Exceptional, (34 reviews)

10/10

Exceptional

(34 reviews)

"It was a cool and wet Memorial Day weekend; the rain was relentless but we had a fine time hanging out at the cozy and charming Upstate Creek House. Clean and comfortable, it made our time in the Shawangunk area quite enjoyable."

Stuart V.

The price is CA $359

CA $359

CA $738 total

includes taxes & fees

Nov 3 - Nov 4

Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.

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 Olivebridge Hotel Reviews

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent

"It was an amazing stay at Catskill Mountain Club. I recommend everyone to visit this property."

Murshed Bin Asad 2-night trip

Posted 1 hour ago

Kaatskill Mountain Club & Condos by Vail Resorts

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent

"We've stayed here on several occasions and have never been disappointed. Just hope that one day in the future they build a pool."

Noel 1-night trip

Posted 2 hours ago

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Courtyard by Marriott Kingston

10/10 Excellent

"Really nice property. The bed was actually comfortable. Will stay again."

Kwadwo A 1-night trip

Posted 4 hours ago

Courtyard by Marriott Kingston

Americas Best Value Inn New Paltz

10/10 Excellent

"Easy parking and great service throughout"

Clarissa 1-night trip

Posted 5 hours ago

Americas Best Value Inn New Paltz

Kingston Regency Inn

10/10 Excellent

"Kind clean quiet good staff"

Tara 2-night trip

Posted 5 hours ago

Kingston Regency Inn

Hunter Lodge, a Bluebird by Lark

10/10 Excellent

"Love the spacious room"

Shuer 1-night trip

Posted 7 hours ago

Hunter Lodge, a Bluebird by Lark

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"It is very close to the FDR Homa and Museum and the Vanderbilt Mansion which was the reason we went to Hyde park. The room was incredibly dark and cramped"

Lorraine 2-night trip

Posted 23 hours ago

Quality Inn Hyde Park Poughkeepsie North

Howard Johnson by Wyndham Saugerties

8/10 Good

"The room was clean & the bed was comfortable. The area is very safe. They didn't have breakfast, just coffee. I will definitely stay here again."

Joan 1-night trip

Posted 1 day ago

Howard Johnson by Wyndham Saugerties

Hotel Kinsley

8/10 Good

"The breakfast could have been better."

David 2-night trip

Posted 1 day ago

Hotel Kinsley

Find out more about Olivebridge

Olivebridge Vacation Homes information

Number of reviews	400
Accommodation	671 Vacation Homes
Lowest Price	CA $213
Highest Price	CA $2,729

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Book Vacation Homes in Olivebridge on Expedia.com

Olivebridge Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Olivebridge vacation homes

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

2. Hot Tub * Fireplace * Close To Woodstock

3. Historic Cottage * Steam Shower * Chef’s Kitchen

4. Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

5. Stone Ridge Modern Mountain House

6. The Studio at the Inn at High Falls

7. Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!

8. NEW: Family Retreat * Fireplace * Spa Bathroom

9. LONGVIEW FARM - Reimagined Modern Farmhouse

10. Hot Tub * Stylish Family Home * 2nd Guest Suite

11. Woodstock Historic Artist Estate - The Carriage House

12. Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

13. Campfire Cottage: Fireplace, fire pit & no chores!

14. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

15. Glamping Tent & Campsite by Minnewaska State Park

16. Woodstock Historic Artist Estate - The Museum House

17. Retro Retreat: renovated 2BR, desk, no chore list!

18. The Loft At The Inn At High Falls

19. Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

20. Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.

Find vacation rentals that suit your style

Top Olivebridge Hotel Reviews

Kaatskill Mountain Club & Condos by Vail Resorts

Find out more about Olivebridge

Olivebridge Vacation Homes information

Explore a world of travel with Expedia