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Our top choices for Bloomington holiday homes

A wooden gate leading to a driveway with a stone pathway, surrounded by greenery and a house in the background.

A building with a blue door and a white facade.

A modern living room with a sofa, armchairs, a coffee table, and a rug.

A hallway with a wooden floor, a rug, a metal rack, and a door on the right.

1. Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm

Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm

Ulster Park

9.8 out of 10, Exceptional, (20 reviews)

9.8/10

Exceptional

(20 reviews)

"Easy access and checkout, extremely clean, accurate pictures, comfy beds, well stocked kitchen. Great for groups. Would gladly stay again!"

Emily F.

The price is NZ$1,422

NZ$1,422

includes taxes & fees

15 Oct - 16 Oct

Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm

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

A compact kitchen with a dining area, a TV, and a window with a view of greenery.

2. 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 NZ$461

NZ$461

includes taxes & fees

3 Nov - 4 Nov

Campfire Cottage: Fireplace, fire pit & no chores!

A modern living room with a sofa, a coffee table, and a dining table. There are two doors, one black and one white, and a window with blinds.

A modern house entrance with a dark door, a staircase, and a light fixture above.

A bedroom with a large bed, a dark double door, a radiator, a small potted plant, and a view into the adjacent room.

A dining area with a round table, black chairs, and a potted plant.

3. Hot Tub - Hammock- Games - Grill - Large Colonial

Hot Tub - Hammock- Games - Grill - Large Colonial

Kingston

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"We had a great stay! Great location and was clean and comfortable for all of our friends."

Amanda R.

The price is NZ$946

NZ$946

includes taxes & fees

20 Oct - 21 Oct

Hot Tub - Hammock- Games - Grill - Large Colonial

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

A kitchen with wooden countertops, a dining table, and chairs. There are jars and cups on the counter.

A living room with a sofa, a small table, a fireplace, a staircase, and a painting on the wall.

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

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, (5 reviews)

10/10

Exceptional

(5 reviews)

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

Tarun

The price is NZ$521

NZ$521

includes taxes & fees

1 Nov - 2 Nov

Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

A hot tub on a wooden deck with a view of a river and trees.

A living room with two sofas, a coffee table, and a large window with a view of trees.

A room with large windows overlooking a lake, a sofa, a lamp, and a small table.

A house with a deck and a pond in front.

5. Welcome to The Boathouse! Waterfront/Boats/Hot tub

Welcome to The Boathouse! Waterfront/Boats/Hot tub

New Paltz

9.6 out of 10, Exceptional, (12 reviews)

9.6/10

Exceptional

(12 reviews)

"We enjoyed our stay very much! Everything was as described, inside was very clean, host was excellent with communication. Scenic, serene spot!"

Jessica B.

The price is NZ$718

NZ$718

includes taxes & fees

13 Oct - 14 Oct

Welcome to The Boathouse! Waterfront/Boats/Hot tub

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

A kitchen with grey cabinets, a coffee machine, and a glass display cabinet above the sink.

A living room with a fireplace, a bookshelf, a sofa, and a coffee table.

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

6. 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 NZ$1,686

NZ$1,686

includes taxes & fees

27 Oct - 28 Oct

NEW: Family Retreat * Fireplace * Spa Bathroom

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

A small, single-story house with a yellow front door, a front porch, and a small front yard with a tree and a bush.

7. 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, (6 reviews)

10/10

Exceptional

(6 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 NZ$435

NZ$435

includes taxes & fees

14 Oct - 15 Oct

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

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

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

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

A modern kitchen with stone walls, a wooden staircase, and a view into the dining area.

8. 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 NZ$889

NZ$889

includes taxes & fees

3 Nov - 4 Nov

Historic Cottage * Steam Shower * Chef’s Kitchen

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

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.

A modern dining area with a round white table, yellow chairs, and a minimalist decor.

9. 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 NZ$535

NZ$535

includes taxes & fees

2 Nov - 3 Nov

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

A modern kitchen with a central island, stainless steel appliances, and a view of greenery outside.

A living room with two leather armchairs, a wooden coffee table, a flat-screen TV, and a decorative cabinet.

A living room with a sectional sofa, two leather armchairs, a round coffee table, and a patterned rug.

A modern kitchen with white cabinetry, a central island, and a dining area with wicker chairs.

10. Trail-front Hudson Valley Retreat in Rosendale

Trail-front Hudson Valley Retreat in Rosendale

Rosendale

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Great location and the house is kept very well with attention to detail in terms of furnishings and things you need in a home. Kitchen has all the condiments and the cooking stuff. Patio has a great grill and if you are in the mood to cook a meal at home it is very much possible."

Sandee S.

The price is NZ$1,656

NZ$1,656

includes taxes & fees

14 Oct - 15 Oct

Trail-front Hudson Valley Retreat in Rosendale

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 spacious room with a wooden staircase, a large window, and a dining area.

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.

11. 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 NZ$634

NZ$634

includes taxes & fees

12 Oct - 13 Oct

The Loft At The Inn At High Falls

A spacious living area with a dining table, sofa, and large windows offering a view of the outdoors.

A spacious room with a wooden staircase, a concrete bench with a dog bowl, and a large window with a view of trees.

A modern living room with a sofa, coffee table, and artwork on the wall.

A window with a view of a wooden deck and trees.

12. 3BR Modern Home in Kingston - Sleeps 6 -Fire Pit -Game Room -Pet Friendly

3BR Modern Home in Kingston - Sleeps 6 -Fire Pit -Game Room -Pet Friendly

Kingston

8.4 out of 10, Very good, (5 reviews)

8.4/10

Very good

(5 reviews)

"Beautiful home, had everything we needed for a great long weekend. Easy to get to town. Highly recommend! Amanda was very clear about the check-in and check out process. Would love to stay again when the weather is warmer."

Mitch B.

The price is NZ$1,198

NZ$1,198

includes taxes & fees

19 Oct - 20 Oct

3BR Modern Home in Kingston - Sleeps 6 -Fire Pit -Game Room -Pet Friendly

A hot tub in a natural setting with a tree and a body of water.

A covered porch with a sofa, a chair, a lamp, and a picture on the wall.

A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden countertop.

A modern kitchen with dark cabinets, stainless steel appliances, a wooden island, and a grey sofa.

13. Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub

Lake Katrine

10.0 out of 10, Exceptional, (17 reviews)

10/10

Exceptional

(17 reviews)

"A nice relaxing spot."

Darren F.

The price is NZ$794

NZ$794

includes taxes & fees

20 Oct - 21 Oct

Peaceful Riverfront Cottage with Private Hot tub

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

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.

A covered outdoor pool area with a view of a forest, furnished with sofas and a table.

14. 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 NZ$1,747

NZ$1,747

includes taxes & fees

29 Oct - 30 Oct

Hot Tub * Stylish Family Home * 2nd Guest Suite

An outdoor seating area with a grill, chairs, and a fire pit surrounded by gravel and trees.

A modern two-story cabin with a large glass front, surrounded by a forested landscape.

A modern bathroom with a toilet, a washing machine, a sink, a large window, and a flat-screen TV mounted on the wall.

A modern living room with a sectional sofa, two wooden side tables, and a large abstract wall art piece.

15. Wynaar Geode Huis | Scandinavian-Style Cabin Near Minnewaska

Wynaar Geode Huis | Scandinavian-Style Cabin Near Minnewaska

Kerhonkson

The price is NZ$1,241

NZ$1,241

includes taxes & fees

3 Nov - 4 Nov

Wynaar Geode Huis | Scandinavian-Style Cabin Near Minnewaska

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

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.

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

16. 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.

Stone Ridge Modern Mountain House

A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

A modern kitchen with a marble countertop, wooden cabinets, and a dining area with a glass table and stools.

A wooden staircase with a black railing leading to a door with a decorative glass panel.

A modern living room with a sofa, a TV, and a dining area with a table and chairs.

17. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"

Nicole Y.

The price is NZ$752

NZ$752

includes taxes & fees

14 Oct - 15 Oct

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

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 two-story building with a wooden exterior, a visible staircase, and a chimney.

18. 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, (45 reviews)

10/10

Exceptional

(45 reviews)

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

Sueane

The price is NZ$426

NZ$426

includes taxes & fees

28 Oct - 29 Oct

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

A staircase leading to a second floor, a sofa with a throw blanket, a floor lamp, a small table with a vase of sunflowers, and a kitchen area visible through an archway.

A spacious living area with a wooden dining table, chairs, a large rug, and a ceiling fan.

A living room with a sofa, a round wooden coffee table, a fireplace, and a bookshelf.

An outdoor deck with a table set for dining, a barbecue grill, and a large umbrella providing shade.

19. Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

New Paltz

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"Superb property - comfortable, spotless, all the amenities you could need, and lots of space. "

Thomas B.

Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

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

A modern outdoor deck with a pool, lounge chairs, and a covered seating area.

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

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

20. 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 NZ$1,687

NZ$1,687

includes taxes & fees

2 Nov - 3 Nov

Hot Tub * Fireplace * Close To Woodstock

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 Bloomington Hotel Reviews

Kingston Regency Inn

10/10 Excellent

"Good"

Arun 1-night trip

Posted 1 hour ago

Kingston Regency Inn

SureStay Plus Hotel by Best Western Highland Poughkeepsie

8/10 Good

"Good: variety for breakfast, spacious parking, courteous staff members, clean rooms, location. To improve: better mattress and pillows."

Mayra 4-night trip

Posted 7 hours ago

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent

"Guest room was designed well. Very clean. Comfortable bed. Great shower, strong pressure, like a massage. Breakfast was excellent , fresh and hot. Will be back"

Norman 1-night trip

Posted 18 hours ago

Hyatt Place Poughkeepsie / Hudson Valley

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"Good breakfast. Friendly helpful staff."

George 1-night trip

Posted 22 hours ago

Quality Inn Hyde Park Poughkeepsie North

Hampton Inn & Suites Poughkeepsie

10/10 Excellent

"Very pleasant stay. Nice breakfast and very cheerful and helpful staff."

Daniel 2-night trip

Posted 22 hours ago

Hampton Inn & Suites Poughkeepsie

Quality Inn Poughkeepsie

8/10 Good

"We only stayed one night , but room was clean and staff pleasant. In the morning we walked about 7 minutes to a nice coffee shop. Location is good . Would stay again."

stacey 1-night trip

Posted 1 day ago

Quality Inn Poughkeepsie

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent

"Amazing hotel right across from the culinary institute of America and close to the FDR library. Andrew was super helpful as was all the staff. Very clean."

Becky 2-night trip

Posted 1 day ago

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent

"Very clean and quiet hotel. The bed was vey comfortable, spacious and clean. I only stayed for 1 night but will definitely come back."

Elaine 1-night trip

Posted 2 days ago

DoubleTree by Hilton Poughkeepsie Convention Center

Red Roof Inn PLUS+ Poughkeepsie

10/10 Excellent

"Very clean hotel and friendly staff."

Juan Carlos 4-night trip

Posted 5 days ago

Red Roof Inn PLUS+ Poughkeepsie

Find out more about Bloomington

Bloomington Holiday Homes information

Number of reviews	219
Accommodation	471 Holiday Homes
Lowest Price	NZ$426
Highest Price	NZ$1,747

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Bloomington on Expedia.com

Holiday Homes in Bloomington

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Bloomington holiday homes

1. Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm

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

3. Hot Tub - Hammock- Games - Grill - Large Colonial

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

5. Welcome to The Boathouse! Waterfront/Boats/Hot tub

6. NEW: Family Retreat * Fireplace * Spa Bathroom

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

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

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

10. Trail-front Hudson Valley Retreat in Rosendale

11. The Loft At The Inn At High Falls

12. 3BR Modern Home in Kingston - Sleeps 6 -Fire Pit -Game Room -Pet Friendly

13. Peaceful Riverfront Cottage with Private Hot tub

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

15. Wynaar Geode Huis | Scandinavian-Style Cabin Near Minnewaska

16. Stone Ridge Modern Mountain House

17. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

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

19. Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

20. Hot Tub * Fireplace * Close To Woodstock

Find holiday rentals that suit your style

Top Bloomington Hotel Reviews

Kingston Regency Inn

Find out more about Bloomington

Bloomington Holiday Homes information

Explore a world of travel with Expedia