Rupert Holiday Rentals, Vermont: Private House Rentals

A rural landscape with a barn on a hill, surrounded by autumn-colored trees.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Rupert

Pet friendly

Apartment

Pool

Condo

Spa

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Rupert hotels

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.

1. Hampton Inn and Suites Manchester

Manchester Center

Rosemary

4.718.740 ₫

5.190.614 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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

An aerial view of a residential area with multiple houses, a tennis court, and a golf course.

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.

2. The Palmer House Resort, an Ascend Collection Hotel

Manchester Center

Elena

2.681.446 ₫

3.378.577 ₫ total

includes taxes & fees

30 Sept - 1 Oct

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

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

3. The Manchester View

Manchester Center

3.125.703 ₫

3.438.273 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

A two-story white building with a red roof, a small porch, and a signboard in front.

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.

4. Four Winds Country Motel

Manchester Center

Catharina

3.486.600 ₫

3.835.260 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.

A spacious living room with a wooden staircase, a television, a sofa set, and a fireplace.

A building with a covered outdoor area, wooden benches, and potted plants.

A living room with a sofa, a coffee table, a chess table, a TV, and a gaming console.

5. Brittany Motel

Manchester Center

Robert

2.237.290 ₫

2.461.019 ₫ total

includes taxes & fees

28 Sept - 29 Sept

A modern living room with a wooden dining table, sofa, and fireplace.

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

A spacious room with wooden floors, large windows, and black yoga mats.

An outdoor dining setup with a view of mountains and trees.

6. Aspen At Manchester

Manchester Center

Ina

2.790.450 ₫

3.355.235 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A cozy indoor space with a chalkboard sign advertising free fire entertainment from 7pm to 9pm.

A cozy interior with a fireplace, wooden furniture, and a large window offering a view of the city at night.

A swimming pool with a clear blue water, surrounded by green grass and tall trees.

A modern building with a glass facade, a brick exterior, and a metal roof.

7. Toll Road Inn

Manchester Center

Steve

3.931.200 ₫

4.324.320 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A large red barn and a white house with a porch, surrounded by trees and a well-maintained lawn.

A cozy living room with a fireplace, bookshelves, and comfortable seating.

A wooden-paneled room with a white sofa, a red pillow, a dark wooden cabinet, and a television mounted on the wall.

A swimming pool with lounge chairs, a red building with a tower, and lush greenery.

8. The Inn at Manchester

Manchester Village Historic District

Reagan

5.967.000 ₫

7.548.580 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A mountain with autumn foliage and a bridge in the foreground.

A room with four light-colored armchairs arranged around a wooden coffee table, a stone wall with a shelf, and a framed map on the wall.

A cozy restaurant with wooden tables and chairs, a kitchen area, and a 'GATHER' sign on the wall.

A circular seating arrangement with Adirondack chairs around a central fire pit, set on a gravel area with a grassy field and trees in the background.

9. Aerie Inn of Vermont

East Dorset

Marianne

2.831.400 ₫

3.086.200 ₫ total

includes taxes & fees

28 Sept - 29 Sept

A cozy living room with two sofas, a coffee table, and a lamp. There is a wooden ceiling with exposed beams and a ceiling fan.

A cozy living room with wooden furniture, a coffee table, and a fireplace.

A welcoming entrance with a 'WELCOME' sign, a red door, and various seasonal flowers and decorations.

A traditional chalet with a sloped roof, flower boxes on the balcony, and a star-shaped emblem.

10. The Olympia Lodge

Manchester Center

Matheus

5.174.000 ₫

5.691.400 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A restaurant with tables set for dining, chairs, and a fireplace in the background.

A two-story building with a porch, American flag, and two white rocking chairs.

A room with a brown leather sofa, a wooden chest labeled "The Honorable Lieutenant Captain Greenwood's Bay," and two windows with floral curtains.

An outdoor dining area with a table set for six, surrounded by wicker chairs, in a garden setting with hanging planters and a lamp post.

11. The Reluctant Panther Inn and Restaurant

Manchester Village Historic District

Jamie

5.954.000 ₫

6.549.400 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A stone fountain surrounded by rocks, with a house in the background.

A covered porch with wooden benches and a swing, white columns, and a view of a street and greenery.

A spacious living area with large windows, a fireplace, and a dining table.

A room with a wooden floor, a patterned rug, a wooden desk with a chair, and a wall clock.

12. Weathervane Motel

Manchester Center

Janet

2.784.600 ₫

3.063.060 ₫ total

includes taxes & fees

28 Sept - 29 Sept

A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

A covered porch with wicker furniture, a white railing, and a view of greenery.

A large, white two-story house with a stone wall and yellow flowers in the foreground.

A traditional bedroom with a four-poster bed, a large bookcase, and a classic wooden floor.

13. The Inn at Ormsby Hill

Manchester Center

Victoria

9.334.000 ₫

10.267.400 ₫ total

includes taxes & fees

27 Sept - 28 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 hotel room with a large bathtub, a bed with a colorful quilt, two bedside lamps, and a framed picture on the wall.

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

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

14. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

2.818.985 ₫

3.227.738 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

A bedroom with a large bed, a wooden dresser, a red chair, a small table with a hookah, and a bathroom visible through an open door.

A room with a wooden desk, a chair, a bed, a TV, and a red wall.

A vending machine and a microwave in a room with tiled flooring.

15. Sunshine Inn

Greenwich

Laura

4.063.969 ₫

4.691.444 ₫ total

includes taxes & fees

25 Sept - 26 Sept

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 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.

16. Sun Lodge near Manchester VT, Ascend Collection Hotel

Bromley Mountain

Mary

3.515.927 ₫

3.867.519 ₫ total

includes taxes & fees

30 Sept - 1 Oct

A two-story house with a porch, a fountain, and a flag.

A large, two-story house with a wrap-around porch, a turret, and a flag.

A cozy living room with a fireplace, a television, a Christmas tree, and a comfortable armchair.

A grand staircase with ornate woodwork, a floral-patterned carpet, and a potted plant.

17. Bentley House Bed and Breakfast

Poultney

nathan

3.835.260 ₫

4.180.433 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

A lobby with a stone fireplace, leather sofas, and a reception desk.

18. The Black Bear Lodge at Stratton Mountain Resort

Stratton

DENNIS

3.770.000 ₫

4.561.700 ₫ total

includes taxes & fees

27 Sept - 28 Sept

Two people sitting by a stone fire pit with a grassy field and mountains in the background.

A hotel room with two single beds, a nightstand with a lamp, and wall decorations of trees.

A welcome sign for Stanford House in Manchester, Vermont.

A two-story building with a red facade and white trim, featuring a garage and a covered porch area.

19. Stanford House

Manchester Center

Julie

2.925.000 ₫

3.514.160 ₫ total

includes taxes & fees

28 Sept - 29 Sept

A swimming pool with a view of a barn and mountains in the background.

A rustic room with wooden floors, a metal cart, shelves with plants, and a refrigerator.

A four-poster bed with a wooden frame, a bench, a small table with a lamp, and a mirror on the wall.

A two-story house with a porch and outdoor seating area.

20. Hill Farm Inn

Arlington

Jennifer

7.774.000 ₫

14.323.920 ₫ total

includes taxes & fees

25 Oct - 26 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Rupert attractions

Merck Forest Farmland Center

Enjoy the mountain views and explore Merck Forest Farmland Center, a lovely green space in Rupert. Discover the spas in this quaint area or seek out its hiking trails.

See properties

Haystack Mountain

Commune with nature and explore the great outdoors at Haystack Mountain during your travels in Rupert. Wander the parks or discover the area's countryside.

See properties

R. K. Kittay Public Library

After visiting R. K. Kittay Public Library, make a plan to see the other sights and activities in Rupert. Wander the parks or discover the area's countryside.

See properties

Learn more about Rupert

Like the countryside? Get away to relaxing Rupert!

See all hotels in Rupert

Top Rupert Hotel Reviews

The Upper Pass Lodge at Magic Mountain

10/10 Excellent

"Dinner was amazing, we arrived on Taco Tuesday and had the best taco and burrito I have ever had. Everyone was very friendly and helpful."

The Manchester View

10/10 Excellent

"Very cool unique setting and property. The bed was like a cloud and very relaxing."

The Equinox Golf Resort And Spa

8/10 Good

"Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better."

Bentley House Bed and Breakfast

10/10 Excellent

"This was such a lovely place. I enjoyed my stay very much, the hosts are so welcoming and made sure I had everything I needed and was comfortable. Breakfast was so nice and I enjoyed the morning conversations."

Four Winds Country Motel

8/10 Good

"Partially updated. Still needs some adjustments but it was clean and comfortable. Breakfast was good."

Weathervane Motel

10/10 Excellent

"The room I had was wonderfully large. It was wry comfortable"

Toll Road Inn

10/10 Excellent

"Great place"

Sun Lodge near Manchester VT, Ascend Collection Hotel

10/10 Excellent

"It was a late check-in after 10 o’clock at night Robin the Night Shift worker made for a pleasant arrival after an exhausting trip. The stay was short, but was very enjoyable and clean."

The Landgrove

10/10 Excellent

"Beautiful room especially with our dog. Outside entrance was a plus! Comfortable bed and chairs. Excellent staff. Every detail was well thought out . We will come again!"

More cheap stays in Rupert

Brittany Motel

1056 Main Street/Historic Route 7A Manchester Center VT

2.237.290 ₫

2.461.019 ₫ total

28 Sept - 29 Sept

includes taxes & fees

Weathervane Motel

2212 Main Street Manchester Center VT

2.784.600 ₫

3.063.060 ₫ total

28 Sept - 29 Sept

includes taxes & fees

6.8/10 (803 reviews)

Aspen At Manchester

5669 Main Street Manchester Center VT

2.790.450 ₫

3.355.235 ₫ total

25 Oct - 26 Oct

includes taxes & fees

8.8/10 Excellent! (691 reviews)

The Manchester View

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

3.125.703 ₫

3.438.273 ₫ total

27 Sept - 28 Sept

includes taxes & fees

9.4/10 Exceptional! (905 reviews)

Four Winds Country Motel

7379 Main Street Manchester Center VT

3.486.600 ₫

3.835.260 ₫ total

25 Oct - 26 Oct

includes taxes & fees

8.4/10 Very good! (561 reviews)

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

4.718.740 ₫

5.190.614 ₫ total

22 Oct - 23 Oct

includes taxes & fees

9.6/10 Exceptional! (1,000 reviews)

Hotels in Rupert with star rating

Frequently asked questions

What's the seasonal weather in Rupert?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Rupert are January, March, November and December, with each month seeing an average of 33 cm of snowfall.

Explore a world of travel with Expedia

Rental cars Rutland Southern Vermont Regional airport

Book Hotels in Rupert on Expedia.com

Find hotels in Rupert, VT from 2.461.019 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Rupert

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Rupert hotels

1. Hampton Inn and Suites Manchester

2. The Palmer House Resort, an Ascend Collection Hotel

3. The Manchester View

4. Four Winds Country Motel

5. Brittany Motel

6. Aspen At Manchester

7. Toll Road Inn

8. The Inn at Manchester

9. Aerie Inn of Vermont

10. The Olympia Lodge

11. The Reluctant Panther Inn and Restaurant

12. Weathervane Motel

13. The Inn at Ormsby Hill

14. The Upper Pass Lodge at Magic Mountain

15. Sunshine Inn

16. Sun Lodge near Manchester VT, Ascend Collection Hotel

17. Bentley House Bed and Breakfast

18. The Black Bear Lodge at Stratton Mountain Resort

19. Stanford House

20. Hill Farm Inn

Stay near popular Rupert attractions

Merck Forest Farmland Center

Haystack Mountain

R. K. Kittay Public Library

Learn more about Rupert

Top Rupert Hotel Reviews

The Upper Pass Lodge at Magic Mountain

The Manchester View

The Equinox Golf Resort And Spa

Bentley House Bed and Breakfast

Four Winds Country Motel

Weathervane Motel

Toll Road Inn

Sun Lodge near Manchester VT, Ascend Collection Hotel

The Landgrove

More cheap stays in Rupert

Brittany Motel

Weathervane Motel

Aspen At Manchester

The Manchester View

Four Winds Country Motel

Hampton Inn and Suites Manchester

Hotels in Rupert with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app