Jamaica Holiday Rentals, Vermont: Private House Rentals

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Go beyond your typical stay in Jamaica

Pet friendly

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Cottage

Family friendly

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Our top choices for Jamaica hotels

A hotel room with two beds, a window with blinds, a desk with a television, and a lamp.

A stone wall surrounding a swimming pool with a metal handrail.

A reception desk with a wooden finish, a small plant, and a seating area with tables and chairs.

A lobby with a leather sofa, a television mounted on the wall, a painting, and a security control panel.

1. The Black Bear Lodge at Stratton Mountain Resort

Stratton

DENNIS

฿4,816

฿5,827 total

includes taxes & fees

17 Sept - 18 Sept

A two-story building with a patio area featuring outdoor seating and a stone fire pit.

A swimming pool with a lifeguard chair, pool lift, and a seating area with chairs and tables.

A treats display with snacks and sundries.

A hotel with a covered entrance, a flagpole with an American flag, and a brick building with multiple windows.

2. Hampton Inn and Suites Manchester

Manchester Center

Tatiana

฿5,149

฿5,664 total

includes taxes & fees

22 Sept - 23 Sept

A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.

A hotel room with two beds, a desk, and a TV.

A two-story white house with a front porch and a garage, surrounded by lush greenery.

A motel with a parking lot, a covered walkway, and a staircase leading to the entrance.

3. The Putney Inn

Putney

JANE

฿3,617

฿3,978 total

includes taxes & fees

20 Sept - 21 Sept

A modern hotel lobby with a wooden herringbone floor, a green wall with 'Chalet 289' signage, a bench with white cushions, and a reception desk with a trash bin and storage baskets.

A wooden deck with a bench and an umbrella, leading to a dark-colored building with a door and windows.

A modern kitchen with a built-in stove, a refrigerator, and a sink. There is a staircase leading to an upper level.

A hotel room with a large bed, a bedside table with a lamp, a desk with a coffee maker, and a view of the outdoors.

4. Chalet 239

West Dover

Michelle

฿3,786

฿4,164 total

includes taxes & fees

23 Sept - 24 Sept

A restaurant with wooden tables and chairs, a central table with a sign reading "The Red Slate Restaurant", and large windows with views of the outside.

A Christmas tree decorated with lights, ornaments, and a bow.

A bar area with a sign reading "MAGIC" and "featured Vermont beers".

A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.

5. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

฿3,041

฿3,482 total

includes taxes & fees

20 Sept - 21 Sept

A cozy room with a sofa, armchair, and round table, decorated with leaf-patterned artwork and a lamp.

A multi-story hotel with balconies, a ski slope in the background, and a clear blue sky.

A dining area with a wooden table and chairs, a window with a view, and a bookshelf with books and decorative items.

A hotel room with a bed, a chair, a table, and a view of mountains through a large window.

6. Sun Lodge near Manchester VT, Ascend Collection Hotel

Bromley Mountain

Terry

฿4,488

฿4,937 total

includes taxes & fees

27 Sept - 28 Sept

A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.

A stone pathway leading to a porch with a wooden railing, surrounded by lush greenery and a lattice fence.

A kitchen with wooden cabinets, a built-in stove, a microwave, and a sink.

A room with a stone fireplace, large windows with curtains, a patterned rug, and a plush chair.

7. Windham Hill Inn

West Townshend

Nadine

฿7,936

฿8,650 total

includes taxes & fees

28 Sept - 29 Sept

A modern living room with a fireplace, large windows, and a cozy seating area.

A large building with a symmetrical facade, a central entrance with a glass door, and two smaller structures on either side.

A modern hotel room with a large bed, a desk, and a chair. There is a window with curtains, a painting of mountains, and a TV on the wall.

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

8. Inn At Mount Snow

West Dover

Barry

฿5,703

฿6,273 total

includes taxes & fees

17 Sept - 18 Sept

A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.

A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.

A hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.

A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.

9. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Daniel

฿5,347

฿5,882 total

includes taxes & fees

20 Sept - 21 Sept

A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

A hotel lobby with a reception desk, seating area, and a wall with framed pictures.

A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.

A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.

10. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Amber

฿4,479

฿4,926 total

includes taxes & fees

20 Sept - 21 Sept

A snow-covered town with a church featuring a clock tower, surrounded by buildings and a mountain in the background.

A porch with white chairs, a glass door, and a dining table with chairs.

A cozy living room with a stone fireplace, a leather sofa, and a coffee table.

11. Vantage Point Villas at Stratton Mountain Resort

Stratton

Kate

฿8,270

฿10,279 total

includes taxes & fees

17 Sept - 18 Sept

A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.

A spacious lobby with a stone wall, a reception desk, and a large window.

A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.

A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.

12. Hampton Inn Brattleboro

Brattleboro

Francesca

฿4,506

฿4,956 total

includes taxes & fees

28 Sept - 29 Sept

A spacious kitchen with wooden cabinets, a large island, and a dining area with floral tablecloths.

A picnic table in a grassy field with a white building with a red roof in the background.

A cozy cabin interior with a fireplace, wooden walls, a checkered chair, and a large window allowing natural light.

A hotel room with a bed, bedside lamps, a telephone, a window with curtains, and an air conditioning unit.

13. Four Winds Country Motel

Manchester Center

Anthony

฿3,856

฿4,241 total

includes taxes & fees

20 Sept - 21 Sept

A calm lake reflecting a forest with autumn foliage.

A hot tub on a covered porch with a view of autumn foliage.

A modern house with a pool, surrounded by lush greenery and mountains in the background.

A house with a balcony and a garden with red flowers.

14. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

฿4,948

฿5,443 total

includes taxes & fees

17 Sept - 18 Sept

A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

A spacious, well-lit kitchen area with modern appliances, a central island with bar stools, and a chandelier.

A hotel room with a bed, a sitting area, a bathroom with a bathtub, and a large mirror.

A hotel room with a bed, a sofa, a coffee table, a desk, and a TV.

15. Best Western Springfield Hotel

Springfield

Gerry

฿5,945

฿6,539 total

includes taxes & fees

17 Sept - 18 Sept

A patio with four wooden chairs and a table set on a stone platform, overlooking a natural landscape with trees and distant hills.

An indoor swimming pool with clear water, surrounded by chairs and a bench.

A spacious dining area with multiple tables and chairs, large windows, and a view of the outdoors.

A modern kitchen with a curved island, bar stools, wine bottles, and a television.

16. The Palmer House Resort, an Ascend Collection Hotel

Manchester Center

Shannon

฿3,431

฿4,323 total

includes taxes & fees

30 Sept - 1 Oct

A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.

A two-story building with a central entrance, a balcony with railings, and a sign indicating it is a lodging and fine dining establishment.

A cozy living room with a stone fireplace, a leather sofa set, a wooden coffee table, and a patterned rug.

A bedroom with a bed, a bedside table, a lamp, a mirror, a dresser, a window, and a ceiling fan.

17. Fullerton Inn

Chester Depot

Kirsty

฿5,613

฿6,118 total

includes taxes & fees

20 Sept - 21 Sept

A spacious, rustic interior with wooden beams, leather furniture, and large windows offering natural light.

A swimming pool with a white fence, lounge chairs, and umbrellas, surrounded by lush greenery and a lake.

The entrance to an Inn & Restaurant with a white door and a sign above it.

A cozy room with a fireplace, wooden beams, a bookshelf, and a television.

18. Farm Road Estate

West Dover

Mark

฿9,290

฿12,045 total

includes taxes & fees

22 Sept - 23 Sept

A pathway leading to a seating area with chairs and a table, surrounded by a grassy field and a forested hill.

A room with a large window, a wooden bench, and a small round table.

A modern bedroom with two beds, a desk, and a chair.

A dining area with a wooden table, chairs, a ceiling light fixture, and artwork on the walls.

19. Otherland Hotel

Newfane

Omar

฿2,825

฿4,132 total

includes taxes & fees

17 Sept - 18 Sept

A bedroom with a fireplace, two beds, a chair, and a nightstand.

A living room with a fireplace, a sofa, a coffee table, a cabinet, and two chairs.

A large, two-story house with a central entrance, surrounded by trees and a mountain backdrop.

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

20. The Manchester View

Manchester Center

Jason

฿3,595

฿3,955 total

includes taxes & fees

21 Sept - 22 Sept

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Where to stay in Jamaica

Find the best Jamaica areas for the activities you enjoy most.

Pikes Falls

While there might not be top attractions in Pikes Falls, you can explore the larger area and discover places like Sunrise Express Ski Lift and Villager Ski Lift.

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Mountain Acres

Though Mountain Acres may not have many top sights, you can venture to the surrounding area to see attractions like Jamaica State Park and Villager Ski Lift.

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East Jamaica

If you're spending some time in East Jamaica, Green Mountain National Forest and West River are top sights worth seeing.

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Stay near popular Jamaica attractions

Jamaica State Park

8.8/10 (5 reviews)

You can take time to visit Jamaica State Park during your travels to Jamaica. Amble around the area's parks or visit its monuments.

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Ball Mountain Dam

Learn about the local history of Jamaica when you take a trip to Ball Mountain Dam. Discover the mountain views in this quaint area or enjoy its ski slopes.

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Margie's Muse Handweaving & Gallery

You can spend an afternoon studying the exhibits at Margie's Muse Handweaving & Gallery in Jamaica. Discover the mountain views in this quaint area or enjoy its ski slopes.

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Hot Glass Works

You can spend an afternoon studying the exhibits at Hot Glass Works in Jamaica. Discover the mountain views in this quaint area or enjoy its ski slopes.

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Ball Mountain State Park

Enjoy a trip to Ball Mountain State Park and popular activities such as skiing in Jamaica. Discover the mountain views in this quaint area.

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Learn more about Jamaica

Tucked along the West River, this charming village offers hiking trails and swimming holes perfect for summer exploration. Visit Jamaica State Park to discover Hamilton Falls or enjoy winter skiing at nearby Stratton Mountain.

See all hotels in Jamaica

A mountainous landscape with autumn foliage, a river, and a small pond.

Top Jamaica Hotel Reviews

The Manchester View

10/10 Excellent

"Great place. Exceeded our expectations. The view, and surroundings are spectacular. And the "continental" breakfast was beyond continental. And it's dog friendly!!!"

Comfort Inn & Suites Brattleboro I-91

8/10 Good

"Great gym. The pools heater was broken so very cold but still nice to have. The breakfast was amazing! Standard room."

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent

"Very clean. Staff were super helpful. Beautiful even though it was “off-season”."

Valley Craft Ales

8/10 Good

"Very basic accommodations, but clean and extremely easy access (just a couple of codes to get in the building and your room). The rooms are basic, and a bit dated, but were clean and a good value for the price. I stayed on a Thursday in mid-September, and it was extremely quiet - very few guests at the hotel, or the bar or restaurant for that matter. If you are staying during high season, I'd definitely follow the recommendation to check for live music in the Inn, since that will be right below the rooms and you will hear it all. Off-season, this was a good choice for us."

Aspen At Manchester

10/10 Excellent

"Absolutely loved this property! Amazing location, super clean and spacious rooms! We loved being in close proximity to the town, which was soooooo amazingly pet friendly! We will definitely be back"

Colonial Motel

8/10 Good

"The room was substantially larger than most motels provide. It was quiet, bed was comfortable. Location was convenient, easy to find and agreeable. Breakfast was very limited— coffee, tea, toast, bagel. Overall, I would stay there again."

The Equinox Golf Resort And Spa

10/10 Excellent

"Great property but a needs a little more tender care."

Hideaway Inn Mt. Snow

10/10 Excellent

"We had a great experience here, well thought out instructions are provided for the electronic check in and room key. No staff (you do not need anyone), very clean and large room. Beautiful property, two very large downstairs living areas with nice amenities (espresso coffee and tea maker), lots of seating and games) and a gorgeous view. Lovely gated on-site pool area. This property is perfect for my dog, who loves to play fetch. Grounds are groomed."

More cheap stays in Jamaica

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT

฿3,595

฿3,955 total

21 Sept - 22 Sept

includes taxes & fees

9.4/10 Exceptional! (896 reviews)

The Putney Inn

57 Putney Landing Rd Putney VT

฿3,617

฿3,978 total

20 Sept - 21 Sept

includes taxes & fees

Latchis Hotel

50 Main Street Brattleboro VT

฿3,640

฿4,004 total

21 Sept - 22 Sept

includes taxes & fees

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

฿4,479

฿4,926 total

20 Sept - 21 Sept

includes taxes & fees

8.6/10 Excellent! (863 reviews)

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

฿4,506

฿4,956 total

28 Sept - 29 Sept

includes taxes & fees

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

฿5,149

฿5,664 total

22 Sept - 23 Sept

includes taxes & fees

9.6/10 Exceptional! (1,000 reviews)

Frequently asked questions

Where is the best place to stay in Jamaica?

Located 20.5 mi (33 km) from the heart of Jamaica, Latchis Hotel is a top choice for your stay, based on our traveller data. Two other options for your visit to the area are Grand Summit Resort, A Vail Resorts Property and Colonial Motel. See all available top hotels, or vacation rentals in Jamaica.

If I need to cancel my hotel reservation in Jamaica, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you booked a non-refundable reservation, it might still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Jamaica.

What are some accommodation options with pools in Jamaica?

The Equinox Golf Resort And Spa: Hotel, 1-minute walk from Green Mountain National Forest. Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Hampton Inn and Suites Manchester and Kimpton Taconic Hotel by IHG are a couple of other choices that offer an on-site pool. View all hotels with pools in Jamaica.

How is it to stay in Jamaica?

Visitors can enjoy all that Jamaica has to offer, including the mountain views, art and monuments. This city also attracts tourists with its small-town vibe. In Jamaica, there are 68 hotels and other accommodation options to choose from. Find out more about Jamaica.

What are the top places to visit in Jamaica?

Cultural venues include Hot Glass Works and Margie's Muse Handweaving & Gallery. Natural beauty is on display at Green Mountain National Forest, Winhall River and West River. A couple of additional sights to add to your itinerary are Jamaica State Park and Ball Mountain State Park. Take a look at what more there is to see and do in Expedia's Jamaica guide.

What's the weather like in Jamaica?

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Jamaica are January, March, November and February, with each month seeing an average of 23 cm of snowfall.

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Book Hotels in Jamaica on Expedia.com

Find hotels in Jamaica, VT from ฿3,397

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Jamaica

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Jamaica hotels

1. The Black Bear Lodge at Stratton Mountain Resort

2. Hampton Inn and Suites Manchester

3. The Putney Inn

4. Chalet 239

5. The Upper Pass Lodge at Magic Mountain

6. Sun Lodge near Manchester VT, Ascend Collection Hotel

7. Windham Hill Inn

8. Inn At Mount Snow

9. Holiday Inn Express Hotel & Suites Brattleboro by IHG

10. Comfort Inn & Suites Brattleboro I-91

11. Vantage Point Villas at Stratton Mountain Resort

12. Hampton Inn Brattleboro

13. Four Winds Country Motel

14. Blue Gentian Lodge at Magic Mountain

15. Best Western Springfield Hotel

16. The Palmer House Resort, an Ascend Collection Hotel

17. Fullerton Inn

18. Farm Road Estate

19. Otherland Hotel

20. The Manchester View

Where to stay in Jamaica

Pikes Falls

Mountain Acres

East Jamaica

Stay near popular Jamaica attractions

Jamaica State Park

Ball Mountain Dam

Margie's Muse Handweaving & Gallery

Hot Glass Works

Ball Mountain State Park

Learn more about Jamaica

Top Jamaica Hotel Reviews

The Manchester View

Comfort Inn & Suites Brattleboro I-91

Grand Summit Resort, A Vail Resorts Property

Valley Craft Ales

Aspen At Manchester

Colonial Motel

The Equinox Golf Resort And Spa

Hideaway Inn Mt. Snow

More cheap stays in Jamaica

The Manchester View

The Putney Inn

Latchis Hotel

Comfort Inn & Suites Brattleboro I-91

Hampton Inn Brattleboro

Hampton Inn and Suites Manchester

Frequently asked questions

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