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Holiday Homes in Bloomington

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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.

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)
"Easy access and checkout, extremely clean, accurate pictures, comfy beds, well stocked kitchen. Great for groups. Would gladly stay again!"
United States
Emily F.
The price is AU$1,181
includes taxes & fees
2 Nov - 3 Nov
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.

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

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is AU$387
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.

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

Hot Tub - Hammock- Games - Grill - Large Colonial
Kingston
10.0 out of 10, Exceptional, (12 reviews)
"We had a great stay! Great location and was clean and comfortable for all of our friends."
United States
Amanda R.
The price is AU$776
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.

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)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is AU$415
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.

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)
"We enjoyed our stay very much! Everything was as described, inside was very clean, host was excellent with communication. Scenic, serene spot!"
United States
Jessica B.
The price is AU$582
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.

6. NEW: Family Retreat * Fireplace * Spa Bathroom

NEW: Family Retreat * Fireplace * Spa Bathroom
Cottekill
10.0 out of 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!"
United States
Shannon M.
The price is AU$1,382
includes taxes & fees
9 Nov - 10 Nov
NEW: Family Retreat * Fireplace * Spa Bathroom
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

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)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is AU$358
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.

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

Historic Cottage * Steam Shower * Chef’s Kitchen
Kingston
10.0 out of 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!!"
United States
Laura D.
The price is AU$700
includes taxes & fees
2 Nov - 3 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.

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)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is AU$447
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.

10. Trail-front Hudson Valley Retreat in Rosendale

Trail-front Hudson Valley Retreat in Rosendale
Rosendale
10.0 out of 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."
United States
Sandee S.
The price is AU$1,324
includes taxes & fees
13 Oct - 14 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.

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)
"this was just a lovely stay all around!! Will absolutely stay there again!"
United States
Inez
The price is AU$503
includes taxes & fees
22 Oct - 23 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.

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)
"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."
United States
Mitch B.
The price is AU$972
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.

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)
"A nice relaxing spot."
United States
Darren F.
The price is AU$624
includes taxes & fees
14 Oct - 15 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.

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)
"Beautiful home, well appointed, hot tub was great, pet friendly, and incredible communication with the hosts! "
United States
Rebecca K.
The price is AU$1,459
includes taxes & fees
2 Nov - 3 Nov
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.

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

Wynaar Geode Huis | Scandinavian-Style Cabin Near Minnewaska
Kerhonkson
The price is AU$1,001
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.

16. Stone Ridge Modern Mountain House

Stone Ridge Modern Mountain House
Stone Ridge
9.6 out of 10, Exceptional, (4 reviews)
"We enjoyed our one night stay. House was very clean and well appointed. Host was responsive. "
United States
Margaret and Greg S.
The price is AU$901
includes taxes & fees
2 Nov - 3 Nov
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.

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)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is AU$610
includes taxes & fees
13 Oct - 14 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.

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)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is AU$349
includes taxes & fees
5 Nov - 6 Nov
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.

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

20. Hot Tub * Fireplace * Close To Woodstock

Hot Tub * Fireplace * Close To Woodstock
West Hurley
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful place! "
United States
Cheryl U.
The price is AU$1,339
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

8/10 Good
"This was my first time at this property. My room was not in the Beekman Arms but in its sister property a few blocks away. The room was large and nicely decorated, it was very clean and the bed was comfortable. The bathroom was very nice and soap, shampoo and towels were supplied in abundance. Breakfast was included and consisted of all sorts of breads, fruit, yogurt, hard boiled eggs, juiced coffee and teas. This was served in a separate building near the residential building Our room was on the third floor so the lack of an elevator pushed my 94 year old body a bit. I would definitely come back to the Beeckman Arms but next time I’ll request a downstairs room."
Steven 1-night trip
Posted 1 hour ago
Beekman Arms and Delamater Inn

Find out more about Bloomington

Bloomington Holiday Homes information

Number of reviews
219
Accommodation
470 Holiday Homes
Lowest Price
AU$349
Highest Price
AU$1,459