Jamaica Holiday Rentals, Vermont: Private House Rentals

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Go beyond your typical stay in Jamaica

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Cottage

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

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

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

Joseph

3.851.054 ₫

4.659.775 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A two-story building with a red facade, a balcony on the second floor, and a parking lot in front.

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

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

2. The Upper Pass Lodge at Magic Mountain

Londonderry

Lynne

2.409.881 ₫

2.759.314 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A cozy room with a fireplace, green sofas, a pool table, and a lamp.

A wooden interior with a dining table set for four, a wooden cabinet with glass doors, and a kitchen area with a refrigerator and cabinets.

A bedroom with a wooden floor, a bed with a white bedspread, a nightstand with a lamp, a dresser, and a television on the dresser.

A deck with white railings overlooking a forested area and a mountain in the distance.

3. Bromley View Inn

Bondville

BARBARA

2.195.876 ₫

2.415.567 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A calm lake reflecting a forest with autumn foliage.

A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

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

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

4. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

3.851.054 ₫

4.236.160 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A wooden triangular structure in a grassy field with a paved path leading to it.

A modern bedroom with a large bed, a desk, and a chair.

A wooden cabin with a sloped roof in a grassy field, a fire pit with chairs, and a path leading to it.

A wall-mounted pegboard with books, a ukulele, and a green towel.

5. Otherland Hotel

Newfane

Omar

3.606.214 ₫

4.747.766 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

A bar area with wooden ceiling, shelves with bottles, and a bar counter.

6. Sun Lodge near Manchester VT, Ascend Collection Hotel

Bromley Mountain

Lynn

2.667.301 ₫

2.934.031 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

A spacious living area with a staircase, a red door, and a large window.

A serene pond with a statue in the center, surrounded by lush greenery and trees.

A living room with leather sofas, a round ottoman, a fireplace, and a bookshelf.

7. Four Columns Inn

Newfane

Raymond

4.047.484 ₫

4.411.757 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A two-story building with a blue exterior, a wooden front porch, and a sign indicating a vacancy.

A bathroom with a double sink, a large mirror, and a bed with a blue patterned bedspread.

A panoramic view of a lake surrounded by forested hills.

A bunk bed with a blue patterned bedspread and a white pillow.

8. Doveberry Inn

West Dover

Veronica

3.140.289 ₫

3.454.318 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

An outdoor seating area with tables and chairs, a large umbrella, and string lights.

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

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

9. Inn At Mount Snow

West Dover

Kenneth

3.600.865 ₫

3.960.952 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A spacious lounge area with multiple seating options, including sofas and chairs, arranged around a central coffee table.

A cozy living room with a stone fireplace, a wooden coffee table, and comfortable seating.

A long dining table with chairs, large windows, and hanging disco balls.

A cozy lounge area with a stone fireplace, comfortable seating, and a 'Hi' sign above.

10. Hideaway Inn Mt. Snow

West Dover

Kailee

2.519.985 ₫

2.771.984 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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

A living room with a sofa, coffee table, and a dining area with chairs and a table. There is a kitchen area with a bar and stools.

An indoor swimming pool with clear lanes, wooden beams, and a 'Stratton' sign.

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

6.435.654 ₫

7.999.518 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A treats display with snacks and sundries.

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

A spacious living area with a fireplace, comfortable seating, and a stone accent wall.

12. Hampton Inn and Suites Manchester

Manchester Center

Rosemary

3.317.334 ₫

3.649.068 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

A modern living room with a dining area, a fireplace, and a television mounted on the wall.

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.

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.

13. Chalet 239

West Dover

Ruth

3.971.187 ₫

4.368.304 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A red building with a stone fire pit and outdoor seating.

A row of red-roofed buildings with a central entrance and a grassy field in the foreground.

A cozy lobby with a stone fireplace, leather sofas, and a staircase.

A pool area with a clear blue pool, surrounded by snow-covered ground and buildings with red and green facades.

14. Grand Summit Resort, A Vail Resorts Property

West Dover

Eben

4.079.268 ₫

4.882.122 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

A living room with a fireplace, a sofa, a coffee table, and a view through a sliding glass door.

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

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

15. The Manchester View

Manchester Center

Jan

2.616.907 ₫

2.878.598 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A large two-story house with a front porch and a well-maintained lawn.

A cozy interior with a bar area, wooden furniture, and a Christmas tree.

A spacious room with high ceilings, wooden beams, large windows, and tables and chairs arranged for dining.

An aerial view of a residential area with houses, a tennis court, and a swimming pool.

16. The Landgrove

Londonderry

Alan

4.921.078 ₫

5.364.078 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A rustic lodge with stone walls, a stone fireplace, and outdoor seating.

A two-story wooden cabin with a stone foundation, large windows, and a wooden porch.

A rustic interior with a stone fireplace, leather sofas, wooden tables, and a large mural on the wall.

A spacious kitchen with wooden cabinets, a large island, and pendant lighting.

17. Seesaw's Lodge

Peru

Michaela

4.066.384 ₫

4.432.358 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A sign for Big Bear's Lodge advertising a heated pool, hot tub, and free WiFi.

A living room with a stone fireplace, a television, a brown sofa, and a wooden coffee table.

A bedroom with a wooden bed, a chair, a desk, a lamp, and a window with curtains.

18. Big Bears Lodge

West Dover

Alfred

4.458.435 ₫

4.904.537 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A snow-covered outdoor area with a white fence, a tree with snow-laden branches, and a building with windows adorned with lights and wreaths.

A hotel room with two beds, a sitting area with a chair and a small table, a television, and a bookshelf.

A room with a window, curtains, a lamp, a chair, a table, and a radiator.

19. 1846 Inn and Tavern

West Dover

Kevin

7.363.525 ₫

8.099.877 ₫ total

includes taxes & fees

24 Oct - 25 Oct

An outdoor patio with green Adirondack chairs, a stone fire pit, and a large planter with flowers.

A cozy cabin-style restaurant with wooden walls, a plaid carpet, and a variety of dishes displayed on shelves.

A large, two-story house with a well-maintained lawn and a stone pathway leading to the entrance.

A sign for the Ritzhof Inn with a vacancy and welcome symbols, a deer sculpture, and a snow-covered roof.

20. Kitzhof Inn

West Dover

David

3.256.596 ₫

3.582.256 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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Where to stay in Jamaica

Find the best Jamaica areas for the activities you enjoy most.Learn more about Jamaica

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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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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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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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 Putney Inn

8/10 Good

"It was adequate"

Latchis Hotel

8/10 Good

"It’s located with restaurants within walking distance. It is well maintained for a historic hotel with probably about 15 steps in the lobby before you get to the elevator. It was noisy some nights due to being in the city and having residents living life. Staff was wonderful. Again location was great to see Buffalo—Niagara is 20 min away, Botanic Garden and Eternal Flame about the same. We enjoyed our stay."

Brittany Motel

8/10 Good

"I liked the clean room and bathroom was reasonably clean. The only staff I encountered was the gentleman who spoke little English cleaning the rooms. The shared kitchen was quite fine, and I can see how dog owners would appreciate the more purposeful backyard dog run/ play area. My only strong complaint is the parking setup, which made it way too tight to park my car on the diagonal (between 2 vehicles that had better, more spacious perpendicular parking) in the corner for Room # 5 (I suspect that they book this room last, as it is the least convenient or assured comfortable assigned/ suggested parking space on the property. Arriving around 8 pm and finding that I could barely (mere inches on both sides) fit my standard RAV4 in this diagonal space was an unnerving / stressful way to arrive and unload. Once I brought in my belongings, I parked further down the line so as to lessen the chances of getting dinged in the morning by the other parked cars. Other than that, the bed was reasonably comfortable and I was happy with the price. Can’t say that I was impressed enough to necessarily stay loyal to this location, though."

The Equinox Golf Resort And Spa

8/10 Good

"The property is a beautiful old hotel, but you can tell they are having a hard time keeping it up. The rooms are big and cozy at the same time, the beds comfortable but the bathroom had some ventilation issues and therefore was a little moldy. While the pool was great, it was a shame the sauna was not working. All in all a nice stay though."

Hampton Inn Brattleboro

10/10 Excellent

"The hotel was fairly new. Coffee was the only thing I felt needed changed."

Kimpton Taconic Hotel by IHG

10/10 Excellent

"The Kimpton Taconic is a beautiful property with professional, friendly staff. We very much enjoyed our stay there and will stay there again the next time we are in Manchester VT."

Colonial Motel

8/10 Good

"The rooms are quite large. There were a lot of unfinished projects going on, so the property was messy and slightly unkempt. The breakfast was terrible. Trash bags were left out attracting skunks. Price made it a 4 star."

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent

"We stayed in room 74-it was beautiful and so clean! From the time we checked in till the time we left, everyone went out of their way to make us feel welcome! The breakfast was delicious! And the gentleman who checked us in was very kind. We would 100% stay there again!!!"

The White House Inn

10/10 Excellent

"The staff was amazing here and we absolutely loved our stay. We will be coming back and staying again."

More cheap stays in Jamaica

The Putney Inn

57 Putney Landing Rd Putney VT

2.174.941 ₫

2.392.436 ₫ total

25 Oct - 26 Oct

includes taxes & fees

8.4/10 Very good! (1,002 reviews)

The Manchester View

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

2.616.907 ₫

2.878.598 ₫ total

3 Nov - 4 Nov

includes taxes & fees

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

2.838.408 ₫

3.122.248 ₫ total

22 Nov - 23 Nov

includes taxes & fees

8.6/10 Excellent! (890 reviews)

Aspen At Manchester

5669 Main Street Manchester Center VT

2.797.830 ₫

3.361.532 ₫ total

2 Nov - 3 Nov

includes taxes & fees

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

3.317.334 ₫

3.649.068 ₫ total

8 Nov - 9 Nov

includes taxes & fees

9.6/10 Exceptional! (1,003 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

3.663.670 ₫

4.030.037 ₫ total

5 Nov - 6 Nov

includes taxes & fees

8.6/10 Excellent! (1,001 reviews)

Hotels in Jamaica with star rating

Frequently asked questions

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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Rental cars Rutland Southern Vermont Regional airport

Book Hotels in Jamaica on Expedia.com

Find hotels in Jamaica, VT from 2.018.801 ₫

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. The Upper Pass Lodge at Magic Mountain

3. Bromley View Inn

4. Blue Gentian Lodge at Magic Mountain

5. Otherland Hotel

6. Sun Lodge near Manchester VT, Ascend Collection Hotel

7. Four Columns Inn

8. Doveberry Inn

9. Inn At Mount Snow

10. Hideaway Inn Mt. Snow

11. Vantage Point Villas at Stratton Mountain Resort

12. Hampton Inn and Suites Manchester

13. Chalet 239

14. Grand Summit Resort, A Vail Resorts Property

15. The Manchester View

16. The Landgrove

17. Seesaw's Lodge

18. Big Bears Lodge

19. 1846 Inn and Tavern

20. Kitzhof Inn

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

Ball Mountain State Park

Hot Glass Works

Learn more about Jamaica

Top Jamaica Hotel Reviews

The Putney Inn

Latchis Hotel

Brittany Motel

The Equinox Golf Resort And Spa

Hampton Inn Brattleboro

Kimpton Taconic Hotel by IHG

Colonial Motel

The Palmer House Resort, an Ascend Collection Hotel

The White House Inn

More cheap stays in Jamaica

The Putney Inn

The Manchester View

Comfort Inn & Suites Brattleboro I-91

Aspen At Manchester

Hampton Inn and Suites Manchester

Latchis Hotel

Hotels in Jamaica with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app