Southern Vermont Holiday Houses

Southern Vermont Holiday Homes
Vermont
United States of America
Holiday Homes
Expedia.co.nz

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

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Our top choices for Southern Vermont holiday homes

A compact bedroom with a bed, a window, and a small kitchenette.

A room with a wooden floor, a red sofa, a white door, a shelf with plants, and a television mounted on the wall.

A room with a red sofa, a wooden table, a vase with flowers, and a window with a view of trees and snow.

A compact kitchen with a microwave, a red couch, and a window.

1. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away

Brattleboro

The price is NZ$186

NZ$186

includes taxes & fees

2 Nov - 3 Nov

Cozy Vermont Tiny Home Get Away

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

A multi-story building with a brick chimney, a snow-covered lawn, and a paved driveway.

A pool area with two hot tubs and a brick patio.

A building with a sign that reads 'Long Trail House.'

2. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton

The price is NZ$457

NZ$457

includes taxes & fees

5 Oct - 6 Oct

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

A kitchen with wooden cabinets, a stainless steel refrigerator, a gas stove, and a built-in oven.

A living room with a floral sofa, a black leather chair, a small table, and a patterned rug.

A small, single-story house with a porch, surrounded by a well-maintained lawn and trees.

3. Cozy Home in Pownal VT

Cozy Home in Pownal VT

Pownal

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."

Jess M.

The price is NZ$366

NZ$366

includes taxes & fees

8 Oct - 9 Oct

Cozy Home in Pownal VT

A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

A two-story white house with a red door, surrounded by autumn foliage and a stone wall.

A kitchen counter with a coffee maker, coffee cups, and a sign that reads 'But first COFFEE'.

4. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment

Dover

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"I loved the super comfy bed and fully stocked coffee cart!"

Ava M.

The price is NZ$259

NZ$259

includes taxes & fees

6 Oct - 7 Oct

The Eagles Wing at The CHM - Private Apartment

A bedroom with a bed, bedside tables, a window, and a radiator.

A kitchen with wooden floors, white cabinets, a central island, and stainless steel appliances.

A modern living room with a flat-screen TV, wooden flooring, a gray sofa, and a kitchen in the background.

A cozy cabin interior with a sectional sofa, a coffee table, a small cabinet, and a window with a view of the outdoors.

5. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

Woodford

The price is NZ$812

NZ$812

includes taxes & fees

6 Oct - 7 Oct

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

A garden with a wooden pergola, purple flowers, and a river view.

A two-story wooden cabin with a balcony, a red door, and a star decoration.

A room with a large window offering a view of a grassy landscape with trees and a distant mountain range.

A living room with a brown sofa, a wooden coffee table, a dining table with chairs, and a staircase in the background.

6. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Putney

9.4 out of 10, Exceptional, (64 reviews)

9.4/10

Exceptional

(64 reviews)

"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"

Susan G.

The price is NZ$464

NZ$464

includes taxes & fees

20 Oct - 21 Oct

Family Friendly Hilltop House In Putney Vermont

A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

A dining area with a long table and chairs, large windows with a view of trees, and a barbecue grill outside.

A cozy room with a wooden table, two blue cushioned chairs, a flat-screen TV, and string lights.

A spacious living area with a high ceiling, wooden beams, a dining table with chairs, a kitchen with modern appliances, and a cozy seating area with a sofa and armchairs.

7. MtSnow* HotTub* Pool * AirHockeyPingPong Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

Wilmington

The price is NZ$1,239

NZ$1,239

includes taxes & fees

28 Oct - 29 Oct

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

A cozy cabin interior with a wooden interior, a fireplace, a sofa, a dining table, and large windows.

A wooden interior with a kitchen area, bar stools, and a dining table.

A modern kitchen with wooden paneling, white cabinets, and a black countertop.

8. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall

9.4 out of 10, Exceptional, (41 reviews)

9.4/10

Exceptional

(41 reviews)

"Our family had a wonderful vacation. The house and location were great. We will come back."

Victoria L.

The price is NZ$1,181

NZ$1,181

includes taxes & fees

21 Oct - 22 Oct

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

A cozy interior with a wooden ceiling, a large window, and a table with chairs.

A cozy room with a dining table set for four, a sofa with checkered cushions, and a large window with curtains.

A spacious kitchen with a central island, wooden cabinetry, and modern appliances.

A cozy cabin interior with a wooden interior, a leather sofa, a pool table, and a large window offering a view of the outdoors.

9. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

Wilmington

10.0 out of 10, Exceptional, (21 reviews)

10/10

Exceptional

(21 reviews)

"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."

Natalie

The price is NZ$975

NZ$975

includes taxes & fees

26 Oct - 27 Oct

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

A room with a large window, a wooden table, two chairs, and a woven basket on the table.

A house with a red door, a welcome sign, and a number 94 on the wall.

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a bar area with metal chairs.

A deck with outdoor furniture, a view of houses, and a mountain in the background.

10. Cozy 3 Bedroom Condo in the Heart of Manchester VT

Cozy 3 Bedroom Condo in the Heart of Manchester VT

Manchester

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Beautiful place Very spacious and super organized we love our stay "

Rafael

The price is NZ$998

NZ$998

includes taxes & fees

4 Oct - 5 Oct

Cozy 3 Bedroom Condo in the Heart of Manchester VT

A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

A person standing on a wooden bridge, holding a cup, with autumn trees and a road in the background.

A multi-story building with a symmetrical facade, large windows, and a central entrance.

A room with a large arched window, a wall-mounted mirror, a wooden dresser, and a table lamp.

11. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia

Dover

10.0 out of 10, Exceptional, (26 reviews)

10/10

Exceptional

(26 reviews)

"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"

Lynn B.

The price is NZ$876

NZ$876

includes taxes & fees

5 Oct - 6 Oct

Modern Mount Snow Gnarvana - Steps to Carinthia

An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

A modern kitchen with a wooden dining table, a chair, and a vase with flowers. There is a living area with a sofa and a lamp.

A street view at dusk with a restaurant and a shop with a mannequin in the window.

A dining area with a wooden table and chairs, a window with a view, and a framed picture on the wall.

12. Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

Manchester

10.0 out of 10, Exceptional, (13 reviews)

10/10

Exceptional

(13 reviews)

"Beautiful cozy house with plenty of beds and space. We drove here in a snowstorm and were so thankful that the host had cleared the driveway and walkways for us. Overall a great stay."

Greg W.

The price is NZ$908

NZ$908

includes taxes & fees

14 Oct - 15 Oct

Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

An aerial view of a house surrounded by a forest with autumn foliage.

A cozy living room with a beige sofa, a wooden coffee table, and two lamps.

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

A kitchen with white cabinets, a granite countertop, and a door leading to another room.

13. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Whitingham

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Great 2 family group vacation spot. Very clean and right in between great ski mountains"

Jonathan

The price is NZ$971

NZ$971

includes taxes & fees

28 Oct - 29 Oct

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

14. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Andover

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Very nice stay. Owners were very gracious. House was clean & comfortable."

Lorraine C.

The price is NZ$1,235

NZ$1,235

includes taxes & fees

6 Oct - 7 Oct

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

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

A wooden tub with a wooden spoon resting on a grassy area near a pond, with a wooden structure in the background.

A house surrounded by autumn foliage with a mountain in the background.

A wooden birdhouse with a door and a small porch, situated near a pond surrounded by trees.

15. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Winhall

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Clean, lots of room, easy access to Stratton, responsive host."

Mark H.

The price is NZ$1,615

NZ$1,615

includes taxes & fees

20 Oct - 21 Oct

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

A house with a deck, two Adirondack chairs, a glass-top table, and a barbecue grill.

West Dover Vacation Rental | 4BR | 4BA | 4,800 Sq Ft | Stairs Required

16. Spacious Vermont Farmhouse | 3 Mi to Mount Snow

Spacious Vermont Farmhouse | 3 Mi to Mount Snow

West Dover

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"All good. "

ken g.

The price is NZ$1,428

NZ$1,428

includes taxes & fees

4 Oct - 5 Oct

Spacious Vermont Farmhouse | 3 Mi to Mount Snow

A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

A spacious living area with a high ceiling, a central island with bar stools, a sofa set, and a staircase leading to an upper level.

A large, two-story house with a prominent gabled roof and a chimney.

An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled floor.

17. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Dover

10.0 out of 10, Exceptional, (13 reviews)

10/10

Exceptional

(13 reviews)

"great location easy access to the mountain and the pool was outstanding."

jim f.

The price is NZ$2,080

NZ$2,080

includes taxes & fees

5 Oct - 6 Oct

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

A wooden staircase leading to a cabin with a balcony, surrounded by trees.

A cozy living room with a fireplace, a large window with curtains, a sofa, and a television mounted above the fireplace.

A kitchen with wooden flooring, a dining area with a table and chairs, and a window with a view of greenery.

A bedroom with a large sliding glass door leading to a balcony with a view of a lake and trees.

18. New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

Wilmington

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Beautiful house and a terrific central location for all things outdoors."

Alex B.

The price is NZ$1,343

NZ$1,343

includes taxes & fees

9 Oct - 10 Oct

New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

A two-story house with a wooden porch, stone steps, and a brown door.

A two-story house with a covered porch, a staircase leading to a deck, and a gravel driveway.

A spacious living room with a large sectional sofa, a wooden coffee table, and a red patterned rug. There are multiple windows providing natural light, and a television mounted on the wall.

19. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

Stratton

10.0 out of 10, Exceptional, (20 reviews)

10/10

Exceptional

(20 reviews)

"Great spot for a large group. "

Brian G.

The price is NZ$1,892

NZ$1,892

includes taxes & fees

26 Oct - 27 Oct

5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

A rustic kitchen with wooden cabinets, a bar area, and a fireplace.

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

A dining area with a wooden table, four chairs, a central vase with flowers, and a view of greenery outside.

20. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home

Manchester

The price is NZ$1,424

NZ$1,424

includes taxes & fees

21 Oct - 22 Oct

1812 House, 2 Stays, 1 home

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 Southern Vermont Hotel Reviews

Hampton Inn Brattleboro

8/10 Good

"The room was clean and spacious."

Wendy 1-night trip

Posted 4 hours ago

Hampton Inn Brattleboro

Inn At Mount Snow

10/10 Excellent

"Clean room, friendly staff, nice views. Best, though, is the relaxing decor, and ambience of the downstairs common area. Very nice. Breakfast is continental and rather simple (ie. cold cereal, yogurt, muffins, fruits) but did the trick for us. Enjoyed our stay. Thank you!"

Lionel 2-night trip

Posted 7 hours ago

Inn At Mount Snow

Colonial Motel

8/10 Good

"I love these kinds of motor lodges and I want them to keep improving and to succeed."

David 1-night trip

Posted 16 hours ago

Colonial Motel

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"Very nice staff and enjoyed my stay."

Charlene 1-night trip

Posted 18 hours ago

Comfort Inn & Suites Brattleboro I-91

Vikings Villages Resort

10/10 Excellent

"Nice place."

Nicolas 2-night trip

Posted 19 hours ago

Vikings Villages Resort

Aspen At Manchester

10/10 Excellent

"Modern, clean, easy access and parking and good location. Touchless check in was easy and efficient."

Joseph 1-night trip

Posted 2 days ago

Aspen At Manchester

The Putney Inn

10/10 Excellent

"Just needed the basics. Putney Inn delivered!"

Gregory 1-night trip

Posted 2 days ago

The Putney Inn

The Equinox Golf Resort And Spa

10/10 Excellent

"Our “go to” for an uber relaxing and comfortable getaway when we are seeking the amenities of an established hotel."

Deborah 1-night trip

Posted 2 days ago

The Equinox Golf Resort And Spa

Hideaway Inn Mt. Snow

10/10 Excellent

"I appreciate the fact that the staff help me out with checking in early. Thank you so much"

Czarian 1-night trip

Posted 2 days ago

Hideaway Inn Mt. Snow

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Southern Vermont Holiday Homes information

Number of reviews	137
Accommodation	663 Holiday Homes
Lowest Price	NZ$186
Highest Price	NZ$2,080

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Activities in Bennington

Book Holiday Homes in Southern Vermont on Expedia.com

Holiday Homes in Southern Vermont

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southern Vermont holiday homes

1. Cozy Vermont Tiny Home Get Away

2. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

3. Cozy Home in Pownal VT

4. The Eagles Wing at The CHM - Private Apartment

5. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

6. Family Friendly Hilltop House In Putney Vermont

7. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

8. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

10. Cozy 3 Bedroom Condo in the Heart of Manchester VT

11. Modern Mount Snow Gnarvana - Steps to Carinthia

12. Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

13. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

14. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

15. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

16. Spacious Vermont Farmhouse | 3 Mi to Mount Snow

17. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

18. New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

19. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

20. 1812 House, 2 Stays, 1 home

Find holiday rentals that suit your style

Top Southern Vermont Hotel Reviews

Hampton Inn Brattleboro

Find out more about Southern Vermont

Southern Vermont Holiday Homes information

Explore a world of travel with Expedia

7. MtSnow* HotTub* Pool * AirHockeyPingPong Darts