Southern Vermont holiday homes

We found 2,670 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southern Vermont

Showing deals for:13 Nov - 20 Nov

Exterior
Exterior
Sports court
Interior
Exceptional
(82 reviews)

Beautiful Lakeview Log Cabin on 60-Acre Property

Peru

8% off
NZ$37,774
for 7 nights, 1 home
NZ$5,396 per night
includes taxes & fees
Beautiful Lakeview Log Cabin on 60-Acre Property
Dining
Living area
Exterior
Exterior
Exceptional
(6 reviews)

Chalet /Stratton Mountain VT /5 minutes from base/Tesla Charger/5 bedrooms

Winhall

11% off
NZ$5,528
for 7 nights, 1 chalet
NZ$790 per night
includes taxes & fees
Chalet /Stratton Mountain VT /5 minutes from base/Tesla Charger/5 bedrooms
Master 2 Second Floor
A beautiful brook that runs through our lot
Silestone counter top and Hickory cabinets
Summer view from the lake
Exceptional
(100 reviews)

New Lakefront Log Home

Wilmington

12% off
NZ$7,197
for 7 nights, 1 chalet
NZ$1,028 per night
includes taxes & fees
New Lakefront Log Home
Family time!
Let the fun times begin
Living area
The name says it all!
Exceptional
(119 reviews)

What are you wating for - All the powder you need, plus 6 bedroom 5 baths await.

Wilmington

8% off
NZ$11,563
for 7 nights, 1 home
NZ$1,652 per night
includes taxes & fees
What are you wating for - All the powder you need, plus 6 bedroom 5 baths await.
New custom kitchen
Large living room with endless natural light
Exterior
Property grounds
Exceptional
(17 reviews)

Private 6 bedroom Chalet 5min to Mt Snow

Dover

8% off
NZ$15,736
for 7 nights, 1 chalet
NZ$2,248 per night
includes taxes & fees
Private 6 bedroom Chalet 5min to Mt Snow
Two story living room with 70" smarttv, premium directtv and bluetooth turntable
Terrace/patio
Indoor hot tub
Sun or snow, it's quite the show
Exceptional
(10 reviews)

HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake

Wilmington

15% off
NZ$4,228
for 7 nights, 1 chalet
NZ$604 per night
includes taxes & fees
HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake
View of the living area from the loft.
Large windows allowing natural light in.
Upstairs entry to mudroom.
Main level, kitchen and loft.
Exceptional
(16 reviews)

Mountain House near Mount Snow & Stratton w/ 2 Fireplaces, Hot Tub & Sauna

Wardsboro

8% off
NZ$7,727
for 7 nights, 1 cabin
NZ$1,104 per night
includes taxes & fees
Mountain House near Mount Snow & Stratton w/ 2 Fireplaces, Hot Tub & Sauna
View of the Main house living room from the kitchen bar
Main house top floor river room with sounds of the river out the windows.
View of the main house from the creek on the property.
Main house top floor river room with deck overlooking the pool and backyard.
Exceptional
(37 reviews)

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro

7% off
NZ$26,299
for 7 nights, 1 home
NZ$3,757 per night
includes taxes & fees
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Patio chairs and solo stove firepit
Front of the house
Livingroom with a view.
King bed
Exceptional
(14 reviews)

Chalet Mount Snow/Stratton Skiing/hiking

East Dover

7% off
NZ$2,508
for 7 nights, 1 chalet
NZ$358 per night
includes taxes & fees
Chalet Mount Snow/Stratton Skiing/hiking
Dining area, 10 Chairs are now black, Need a new picture!
View out front door
Early morning summer view
 Open Kitchen with a wide open feel
Exceptional
(240 reviews)

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

Wilmington

8% off
NZ$8,582
for 7 nights, 1 home
NZ$1,226 per night
includes taxes & fees
Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews
Exterior
Interior
Dining
Exterior
Exceptional
(54 reviews)

Skylight Ski Lodge VT Rustic Chic Near Stratton

Winhall

8% off
NZ$17,334
for 7 nights, 1 home
NZ$2,476 per night
includes taxes & fees
Skylight Ski Lodge VT Rustic Chic Near Stratton
Exterior
Property grounds
Living area
Room
Exceptional
(23 reviews)

Bear Pass Bunkhouse

Manchester

8% off
NZ$3,737
for 7 nights, 1 home
NZ$534 per night
includes taxes & fees
Bear Pass Bunkhouse
View of loft bedroom
Living room
Upper level
Main living area
Exceptional
(8 reviews)

Family Friendly Stratton Home for All Seasons, 7 min to ski mountain

Winhall

8% off
NZ$15,363
for 7 nights, 1 home
NZ$2,195 per night
includes taxes & fees
Family Friendly Stratton Home for All Seasons, 7 min to ski mountain
Dining
Interior
Private kitchen
Bar (on property)
Exceptional
(77 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

15% off
NZ$14,554
for 7 nights, 1 home
NZ$2,079 per night
includes taxes & fees
Western Mountain Lodge on River and Close to Stratton
Exterior
Living area
Exterior
Exterior
Exceptional
(67 reviews)

Luxury Custom Built Post and Beam

Peru

16% off
NZ$15,276
for 7 nights, 1 home
NZ$2,182 per night
includes taxes & fees
Luxury Custom Built Post and Beam
Terrace/patio
Large open-concept living and kitchen area
Dining area
Bedroom 1: Queen Bed
Exceptional
(17 reviews)

Leonard’s Log Cabin— Mt. Snow/Stratton Ski House

Wardsboro

7% off
NZ$4,822
for 7 nights, 1 cabin
NZ$689 per night
includes taxes & fees
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Back porch
Living area
Front door
View from mudroom
Exceptional
(39 reviews)

Wishing Well Cabin

Jamaica

7% off
NZ$3,904
for 7 nights, 1 cabin
NZ$558 per night
includes taxes & fees
Wishing Well Cabin
Living area
Living area
Interior
Dining
Exceptional
(12 reviews)

Forest Lodge - Near 6 Ski Resorts

Jamaica

8% off
NZ$15,016
for 7 nights, 1 home
NZ$2,145 per night
includes taxes & fees
Forest Lodge - Near 6 Ski Resorts
Games room
Indoor spa tub
Dining
Private kitchen
Exceptional
(53 reviews)

SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.

Wilmington

8% off
NZ$14,132
for 7 nights, 1 home
NZ$2,019 per night
includes taxes & fees
SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.
Outdoor dining
Living area
Exterior
Living area
Exceptional
(112 reviews)

Spacious, Comfortable & Close!!! GOLF TRIPS!

Dover

15% off
NZ$9,170
for 7 nights, 1 home
NZ$1,310 per night
includes taxes & fees
Spacious, Comfortable & Close!!! GOLF TRIPS!
Exterior
Dining
Private kitchen
Interior
Exceptional
(45 reviews)

Bennington Guest Farmhouse

Bennington

8% off
NZ$3,152
for 7 nights, 1 home
NZ$450 per night
includes taxes & fees
Bennington Guest Farmhouse
Master bedroom is 12X20 and overlooks our beautiful river - private bathroom
One of a kind woodwork, beautiful handmade furniture and built ins.....
The tile work in all bathrooms and kitchen are unique hand made tiles
Inside, Outside - take your pick - it's always magical
Exceptional
(53 reviews)

One of a Kind Post and Beam Home on Private 100 acre Island

Jamaica

8% off
NZ$11,261
for 7 nights, 1 home
NZ$1,609 per night
includes taxes & fees
One of a Kind Post and Beam Home on Private 100 acre Island
Interior
Newly renovated kitchen with all major appliance, utensils, pots and pans.
Another view of our dining room and newly renovated kitchen.
Fully enclosed loft space
Exceptional
(9 reviews)

Cozy Cabin - walking distance to town and 10 minutes to Bromley. Pet friendly!

Manchester

11% off
NZ$4,828
for 7 nights, 1 cabin
NZ$690 per night
includes taxes & fees
Cozy Cabin - walking distance to town and 10 minutes to Bromley. Pet friendly!
Stratton mtn fire tower view
Outdoor dining
let it snow!
main entrance
Exceptional
(38 reviews)

Cozy Manchester Getaway with Amazing Views!!!

Winhall

7% off
NZ$5,976
for 7 nights, 1 home
NZ$854 per night
includes taxes & fees
Cozy Manchester Getaway with Amazing Views!!!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Head to the scenic city of Southern Vermont

Enjoy the festivals and other features of Southern Vermont. Travellers to this scenic city praise the skiing, snowboarding and mountain views. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Southern Vermont

Are you searching for attractions to visit while you're in the area? Travellers enjoy Southern Vermont for its skiing, snowboarding and hiking. Venture out of your holiday home and experience everything that Southern Vermont has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Mount Snow (4.4 mi / 7 km)
  • Mount Snow Golf Course (5.1 mi / 8.2 km)
  • The Hermitage Club (6.3 mi / 10.2 km)
  • Stratton Mountain Resort (6.5 mi / 10.5 km)
  • The Hermitage Golf Club (7.8 mi / 12.6 km)
  • Stratton Mountain Golf Course (8.1 mi / 13.1 km)

Exploring the mountains and other natural features in Southern Vermont

Whether you're an adventurous traveller or just want to appreciate the scenery, Southern Vermont is a great place to get outside. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Raponda (9.8 mi / 15.7 km)
  • Hogback Mountain Conservation Area (11.2 mi / 17.9 km)
  • Lye Brook Falls (12 mi / 19.2 km)
  • Harriman Reservoir (12.7 mi / 20.5 km)
  • Mount Equinox (14.3 mi / 23.1 km)
  • Battenkill River (14.4 mi / 23.2 km)

Transport options to and around Southern Vermont

If you prefer train travel, make your way to Brattleboro Station or Bellows Falls Station to see more of the city.

Frequently asked questions

What is the best area to stay in Southern Vermont when booking a holiday home?
Bennington is one of the most preferred areas to book a holiday property in Southern Vermont. Searching for some awesome things to do and see in this destination? Take time to visit Bromley Mountain Ski Resort and Equinox Preservation Trust.
What is the most popular type of holiday home accommodation in Southern Vermont?
Based on our research, houses are the most popular property type in Southern Vermont. But of course, everyone's idea of an awesome trip isn't going to be the same. Bookabach has holiday homes of all sizes, shapes and budgets, so you're sure to find your ideal match.
How much does it cost to rent a holiday home in Southern Vermont?
Different factors influence what you'll pay for your holiday home in Southern Vermont, including the time of year, property type and length of stay. However, all of our holiday homes have something in common — excellent value. Simply add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Southern Vermont?
The average price for a holiday home by the beach in Southern Vermont depends on when you're visiting the area and the size and style of property you're looking for. Find prices easily on Bookabach by entering your preferred travel dates. Then use our handy filter tool to choose the number of bedrooms and amenities essential to you, like air conditioning, a pool and WiFi.
What are popular home amenities in Southern Vermont?
The most popular home amenities guests are looking for in Southern Vermont are a fridge, an oven and a microwave oven. Whether you're taking a trip with your besties, family or even pets, Bookabach holiday homes provide the best amenities for making new memories with the people who matter most.
Are there large group holiday homes in Southern Vermont?
Southern Vermont has 474 holiday homes that can fit 10 or more guests. These properties come with all the space you need to enjoy good times with your favourite people.
What are the top attractions for families in Southern Vermont?
Keep the kids entertained at these fantastic family-friendly attractions in Southern Vermont:
  • Bromley Mountain Ski Resort
  • Magic Mountain Ski Resort
  • Mount Snow
Can I find two-bedroom holiday homes in Southern Vermont?
You can pick from 169 two-bedroom homes in Southern Vermont. Put the kids in the second room or fill it with a couple of your favourite people. There's space for whoever's fortunate enough to be joining in on the fun.
Are there holiday homes with WiFi in Southern Vermont?
Southern Vermont has 495 holiday homes with WiFi, so you can stay connected while you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming TV shows with the family to catching up on social media, these Bookabach homes make it a breeze to get online.
How old do you have to be to rent a holiday home in Southern Vermont?
The minimum required age is usually 16, 18 or 21. It can differ across properties on Bookabach, so check the rules of your chosen Southern Vermont holiday home before booking your trip.
How long can I rent a holiday home in Southern Vermont for?
How long you can rent a holiday home in Southern Vermont is down to the property. Simply enter your preferred dates to see a list of options offering extended stays. With lots of creature comforts such as air conditioning and kitchens, as well as some offering weekly or monthly discounts, you're sure to find someplace just right to call your home away from home in Southern Vermont.

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