Southern Vermont Holiday Rentals, Vermont: Private House Rentals

The Bennington County Court House with a white facade, green shutters, and a gold dome.

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Go beyond your typical stay in Southern Vermont

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Our top choices for Southern Vermont hotels

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

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

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

A treats display with snacks and sundries.

1. Hampton Inn and Suites Manchester

Manchester Center

Rosemary

3.317.334 ₫

3.649.068 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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 chair.

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.

2. The Manchester View

Manchester Center

Jan

2.616.907 ₫

2.878.598 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A hotel with a covered entrance, a clear sky, and a tree in the foreground.

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

A spacious lobby with modern furniture, a large digital map display, and a high ceiling with geometric lighting.

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

3. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Timothy

3.489.210 ₫

3.838.131 ₫ total

includes taxes & fees

22 Nov - 23 Nov

An indoor swimming pool with clear water, metal railings, and lounge chairs.

A hotel lobby with a fireplace, seating area, and a bar.

A hotel room with two beds, a desk with a television, and a window with a mountain view.

A hotel reception area with a reception desk, a chandelier, framed pictures, and a coffee station.

4. Hampton Inn Bennington

Bennington

Josephine

4.005.613 ₫

4.366.118 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

5. Inn At Mount Snow

West Dover

Kenneth

3.600.168 ₫

3.960.184 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

A stone fireplace with a fire, flanked by two leather armchairs and a small table with a plate of food and wine glasses.

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

6. Grand Summit Resort, A Vail Resorts Property

West Dover

Eben

4.078.479 ₫

4.881.177 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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.

7. The Black Bear Lodge at Stratton Mountain Resort

Stratton

Joseph

3.850.309 ₫

4.658.874 ₫ total

includes taxes & fees

27 Oct - 28 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 bunk bed with a blue patterned bedspread and a white pillow.

A bedroom with a bed, dresser, TV, and a chair.

8. Doveberry Inn

West Dover

Veronica

3.139.682 ₫

3.453.650 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

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

An indoor swimming pool with a tiled deck, safety signs, and a few chairs.

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

9. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

2.838.408 ₫

3.122.248 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A spacious kitchen with large windows, a bar area, and a dining setup with chairs and tables.

A large, white colonial-style house with a porch, surrounded by lush greenery and trees.

A spacious restaurant with high ceilings, patterned flooring, and multiple seating areas.

A large, white, two-story house with a central balcony and a covered porch.

10. The White House Inn

Wilmington

Teresa

4.423.979 ₫

4.866.377 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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 two-story white building with a central entrance, double doors, and a porch with railings.

11. 1846 Inn and Tavern

West Dover

Kevin

7.362.101 ₫

8.098.311 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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

A swimming pool with a gazebo, outdoor seating, and a view of trees.

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

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

12. Hideaway Inn Mt. Snow

West Dover

Kailee

2.519.497 ₫

2.771.447 ₫ total

includes taxes & fees

24 Nov - 25 Nov

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

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.

A bedroom with a large bed, bedside tables, a small bench, and a sofa in the corner.

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

13. The Reluctant Panther Inn and Restaurant

Manchester Village Historic District

Jeffrey

5.917.589 ₫

6.509.348 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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

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

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

A bar area with wooden flooring, a leather sofa, and a bar counter with a variety of liquor bottles.

14. The Inn at Manchester

Manchester Village Historic District

Dawn

3.605.517 ₫

4.561.302 ₫ total

includes taxes & fees

5 Nov - 6 Nov

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.

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

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

15. Farm Road Estate

West Dover

Mark

4.996.549 ₫

6.917.734 ₫ total

includes taxes & fees

18 Nov - 19 Nov

A garden with a large rock centerpiece, surrounded by various plants and a wooden structure in the background.

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 spacious dining area with multiple wooden tables and chairs, large windows with curtains, and a wooden ceiling.

16. Big Bears Lodge

West Dover

Alfred

4.457.573 ₫

4.903.589 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

A spacious room with a wooden dining table and chairs, a desk with a lamp, and large windows with curtains.

17. Aspen At Manchester

Manchester Center

Nathan

2.797.830 ₫

3.361.532 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

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

A spacious living room with a fireplace, leather sofa, and a large window offering a view of the outdoors.

A bar area with wooden ceiling beams, bar stools, and a long counter with bottles and glasses.

18. Long Trail House at Stratton Mountain Resort

Stratton

Michael

9.173.555 ₫

11.402.729 ₫ total

includes taxes & fees

5 Nov - 6 Nov

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

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

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.

19. Chalet 239

West Dover

Ruth

3.971.187 ₫

4.368.304 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A wooden interior with a view of a forest through a triangular opening.

A modern living room with a dining area, a sofa set, and a coffee table.

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

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

20. Otherland Hotel

Newfane

Omar

3.606.214 ₫

4.747.766 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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Holiday Rentals in Southern Vermont

Aparthotel

Long Trail House at Stratton Mountain Resort

Stratton

"Clean well, equipped room. Great amenities, wonderful proximity to all the action in the village,easy parking and access throughout the facility."

Apartment

A sauna with wooden walls and multiple sliding glass doors.

A spacious kitchen with a dining area, a built-in fridge, and a loft bedroom with a view.

An indoor swimming pool with a clock, chairs, and windows with a snowy view.

A cozy living room with a gray sectional sofa, a fireplace, and a television mounted on the wall.

Walk to Mount Snow Resort: Unit w/ Pool & Hot Tubs

West Dover

"Great place to stay. Close to the mountain. Well stocked with anything you might need!"

Holiday Home

A spacious living room with a wooden ceiling, large windows, a dining area, and a bookshelf.

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

A wooden deck with a table set for dining, a blue umbrella, and a view of a garden and pool.

A backyard with a swimming pool, surrounded by a wooden deck and a fence.

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Arlington

"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "

Cottage

A small white house with a chimney, a front porch, and a stone wall.

A bedroom with a bed, a chair, a desk, and a window.

A laundry area with two front-loading washing machines, a bench, a trash bin, and a window with a view of trees.

A kitchen with white cabinets, a wooden dining table, and chairs. There is a washing machine and a refrigerator.

12 Mi to Bromley Mtn Ski Resort: Quiet Hideaway

Manchester Center

"Wonderful location, across the road from the mountain and the stream and an old barn. It literally feels like you are in the middle of nowhere. The bedrooms were well appointed, plenty of towels and sheets. There's also a washer and dryer in the kitchen. The hallway light was full of bugs and impossible for us to find the switch to turn it off. The front door is in serious need of repair. The property manager is woefully unskilled at her job."

Apartment

A house with a porch and a view of a snow-covered mountain.

A pool area with a clock, chairs, and tables.

A room with a view of a snowy mountain, a wooden sign reading "MOUNT SNOW", and a wooden floor.

A modern living room with a sofa, a small table, a lamp, and a painting on the wall.

Snow Mountain Condo: Hot Tub + Shuttle to Resort

West Dover

"I was a little hesitant booking as this property had no reviews on Expedia. Our stay was outstanding! Everything well stocked in the kitchen. We cooked every day. Pool And hot tub area was amazing, super clean. Property had an entire shed of firewood for use in the fireplace. Super close to Mt Snow! We shall return."

Apartment

A residential area with a pathway leading to a sports center sign.

A modern kitchen with stainless steel appliances, a dining area with a round table and wooden chairs, and a small island with bar stools.

A sauna room with a hot tub, wooden walls, and a view of greenery outside.

A house with a front porch, a wooden pathway leading to the entrance, and a garden with various plants and flowers.

Comfortable Dover Apartment: Walk to Mt Snow!

West Dover

"Very clean, close to the mountain. 2 bathrooms is a plus."

Cottage

A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

A cozy living room with a sectional sofa, a coffee table, and a television. There is a wooden door leading to a dining area and a kitchen visible in the background.

A house with a deck, surrounded by trees and a grassy slope.

A cozy living room with a stone fireplace, wooden walls, and a television mounted on the wall.

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Wilmington

"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"

Cottage

A covered outdoor seating area with two chairs and a table, overlooking a snowy forest.

A kitchen with wooden beams, a large island, and a dining area with blue upholstered chairs.

A cozy cabin interior with a wooden ceiling, a television on a cabinet, a sofa with cushions, and a door leading outside.

Hiking Trails On-site: Cozy Falls Brook Cabin

Brattleboro

"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"

Cottage

A modern kitchen with wooden cabinets, stainless steel appliances, and a glass dining table.

A covered porch with chairs, a view of a street with houses, and a parked car.

< 1 Mi to Historic District! Retreat in Bennington

Bennington

"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."

Cottage

A stone fireplace with a flat-screen TV above it, a wooden floor, a bed with white bedding, and a view of the outdoors through a window.

A kitchen with a white refrigerator, wooden cabinets, a coffee maker, and a toaster.

A cozy living room with a stone fireplace, wooden flooring, a dining table with chairs, and a mounted television.

A house with a deck, surrounded by trees, with a fire pit and Adirondack chairs.

'mount Pine' Winter Escape Near the Green Mtns!

Wardsboro

"Amazing place! Super clean and cozy, and host was extremely nice and communicative. Highly recommend."

Cottage

A wooden deck with a metal railing overlooking a forested area.

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

A room with a wooden floor, a sofa, a dining table, and several chairs. There is a window with curtains, a framed picture on the wall, and a red sign with the word "BAR" on it.

A room with a wooden barrel bar, leather chairs, a wooden dresser, and a ski patrol sign on the wall.

Wilmington Retreat Near Trails, Skiing & Festivals

Wilmington

"Great location and awesome house. Owners were easy to communicate with. "

Cottage

A cozy cabin interior with a large bear painting, a fireplace, and a wooden dining area.

An indoor swimming pool with wooden beams, a green slide, and lounge chairs.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with stools.

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

Wilmington Retreat w/ Pool 8 Mi to Mount Snow

Wilmington

"What a great property! The fire pit, the basement game room, the kitchen, and the common spaces are all excellent. The process of working through a secondary property management company was slightly cumbersome but once we had the guest contact, Stephanie was great."

Apartment

A spacious room with a large sliding glass door leading to a backyard, a black exercise bike, and a massage table.

Two red Adirondack chairs by a calm lake surrounded by lush greenery.

A white wooden deck with a metal railing overlooking a pond surrounded by trees with autumn foliage.

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

Ambient Manchester Abode w/ Deck & Pond!

Manchester Center

"The Corbett family was warming and welcoming. Their hideaway is right in the middle of Manchester and is very easy to walk to all different restaurants such as the Crooked Ram and Seasons. The grounds of the property were beautiful and relaxing. Will certainly be going back! "

Apartment

A spacious living room with a fireplace, wooden walls, a staircase, and a blue sofa.

A cozy living room with a blue sectional sofa, a round coffee table with a book and flowers, and a large window with curtains.

A wooden deck with a bench and a chair, overlooking a row of beach houses with a sign that reads "MT SNOW".

A wooden interior with a 'welcome' sign, a bench, a coat rack, and a door labeled 'SKI'.

Relaxing Mountain Refuge: 4 Miles to Mt Snow!

West Dover

"Amazing stay, great hosts, will be back here next time in the area"

Apartment

A modern kitchen with wooden cabinets, a built-in microwave, and a dining area with a wooden table and chairs.

A hallway with a wooden door, a welcome sign, a coat rack, and a small black storage unit.

A living room with a sofa, chairs, a coffee table, and a large window.

A two-story house with a stone retaining wall, a wooden deck, and a paved driveway.

Cozy Ski-in/ski-out Condo on Magic Mountain

Londonderry

"This was an outstanding location. The beds and pillows were insanely comfy and the couch was, too. Rare to find a place that is this comfortable. There was plenty of parking and it was nice and quiet. Hard to imagine a more pleasant stay. Appreciated the text outreach to make sure I had all the information I needed before I arrived, too. "

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Stay near popular Southern Vermont attractions

Stratton Mountain Resort

9.2/10 (365 reviews)

Stratton Mountain Resort offers 99 trails across 2,003 feet of vertical terrain for winter sports. Enjoy year-round adventures from skiing to golf and mountain biking in southern Vermont's premier outdoor playground.

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Skiers on a snowy slope with a ski lift in the background.

Mount Snow

9.2/10 (568 reviews)

This southern Vermont retreat offers 86 trails across four mountain faces for winter thrills. In summer, the resort transforms with downhill mountain biking, hiking trails, and an 18-hole championship golf course.

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A mountainous landscape with a forested area covered in snow.

Bromley Mountain Ski Resort

8.8/10 (160 reviews)

Hit the slopes in Peru with a visit to Bromley Mountain Ski Resort. Discover the mountain views in this quaint area.

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A calm lake reflecting a forest with autumn foliage.

Emerald Lake State Park

You can take time to visit Emerald Lake State Park during your travels to East Dorset. Discover the mountain views in this quaint area.

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Magic Mountain Ski Resort

8.6/10 (74 reviews)

Magic Mountain delivers an authentic Vermont skiing experience with challenging terrain and a community vibe. Enjoy steep slopes and extensive glades, then unwind at the cosy Black Line Tavern après-ski scene.

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Golf Club at Equinox

8.4/10 (29 reviews)

This historic Walter Travis-designed course unfolds against Vermont's majestic Green Mountains. Enjoy undulating greens and mountain vistas before relaxing at the Dormy Grill overlooking the ninth hole.

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Vermont Country Store

9.2/10 (382 reviews)

This nostalgic emporium showcases hard-to-find treasures from vintage toys to classic penny sweets. Browse both levels for unique Vermont-made goods while experiencing authentic New England charm.

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Stratton Mountain Summit Gondola

9.4/10 (98 reviews)

Glide to southern Vermont's highest peak for panoramic views spanning four states. At the summit, explore hiking trails, climb the historic fire tower, or simply bask in the breathtaking mountain landscape.

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Learn more about Southern Vermont

Covered bridges and quaint villages dot the landscape, inviting you to explore charming towns like Manchester and Bennington. Hike part of the Appalachian Trail, or hit the slopes at Mount Snow for year-round outdoor adventures.

See all hotels in Southern Vermont

A covered bridge with a sign indicating a height restriction of 10 feet 6 inches.

Top Southern Vermont Hotel Reviews

The Manchester View

10/10 Excellent

"Great place and clean..Uber is not available fyi"

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."

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 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."

Comfort Inn & Suites Brattleboro I-91

8/10 Good

"Was a good room for a one night stay on a road trip."

More cheap stays in Southern Vermont