Southern Vermont holiday homes

We found 2,677 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southern Vermont

Showing deals for:25 Dec - 1 Jan

Private kitchen
Property grounds
Property grounds
Room
Exceptional
(11 reviews)

the farmhouse at Big Picture Farm

Townshend

13% off
NZ$37,668
for 7 nights, 1 room
NZ$5,381 per night
includes taxes & fees
the farmhouse at Big Picture Farm
Indoor hot tub
Terrace/patio
Two story living room with 70" smarttv, premium directtv and bluetooth turntable
Exterior
Exceptional
(10 reviews)

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

Wilmington

17% off
NZ$31,166
for 7 nights, 1 chalet
NZ$4,452 per night
includes taxes & fees
HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake
Deer Room - 1st floor bedroom with a queen bed.
Fully stocked kitchen with plenty of room to prepare a family dinner
The first floors open plan is great for large groups.
Bear Room - 2nd Floor bedroom with a king bed, tv with roku and sitting area.
Exceptional
(11 reviews)

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Chester

8% off
NZ$7,977
for 7 nights, 1 chalet
NZ$1,140 per night
includes taxes & fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Adults upstairs & kids in Gameroom hangout TV, DVD, VCR & large movie library
Morning coffee on the front deck overlooking our wooded lot?
Beautiful 4-season ski chalet on Okemo less than a mile to ski base
Game room with air hockey, 2nd sectional and gas fireplace. Bathroom with tub
Exceptional
(133 reviews)

Okemoskichalet with Game Room & Hot Tub on Okemo Mt. 1 mile to base! Sleeps 12

Ludlow

8% off
NZ$13,301
for 7 nights, 1 chalet
NZ$1,900 per night
includes taxes & fees
Okemoskichalet with Game Room & Hot Tub on Okemo Mt. 1 mile to base! Sleeps 12
Summer view from the lake
A beautiful brook that runs through our lot
Silestone counter top and Hickory cabinets
Enjoy chess, checkers or backgammon
Exceptional
(101 reviews)

New Lakefront Log Home

Wilmington

12% off
NZ$10,271
for 7 nights, 1 chalet
NZ$1,467 per night
includes taxes & fees
New Lakefront Log Home
King bed
Front of the house
Livingroom with a view.
Patio chairs and solo stove firepit
Exceptional
(16 reviews)

Chalet Mount Snow/Stratton Skiing/hiking

East Dover

8% off
NZ$10,082
for 7 nights, 1 chalet
NZ$1,440 per night
includes taxes & fees
Chalet Mount Snow/Stratton Skiing/hiking
Dining
Private kitchen
Interior
Living area
Exceptional
(7 reviews)

Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY

Cropseyville

8% off
NZ$19,399
for 7 nights, 1 home
NZ$2,771 per night
includes taxes & fees
Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY
3-Season porch (new addition 2023)
Large open-concept living and kitchen area
Dining area
Terrace/patio
Exceptional
(18 reviews)

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

Wardsboro

8% off
NZ$18,150
for 7 nights, 1 cabin
NZ$2,593 per night
includes taxes & fees
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Dining
Terrace/patio
Living area
Private kitchen
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

16% off
NZ$5,547
for 7 nights, 1 cottage
NZ$792 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Private kitchen
Property grounds
Exterior
Living area
Exceptional
(28 reviews)

Bear Pass Bunkhouse

Manchester

8% off
NZ$3,883
for 7 nights, 1 home
NZ$555 per night
includes taxes & fees
Bear Pass Bunkhouse
Light filled kitchen
Front of house, early spring
Private driveway with ramp to enter house. Gently babbling stream in the front
Bedroom #2 Queen bed with large windows & french doors
Exceptional
(7 reviews)

Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible

Weston

8% off
NZ$7,511
for 7 nights, 1 home
NZ$1,073 per night
includes taxes & fees
Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible
Living area
Pool in the nearby recreational building
Living area
Dining
Exceptional
(140 reviews)

Mountain Paradise—SKI-ON/SKI-OFF Okemo Ski Getaway ⛷ hot tubs, pool, fireplace

Ludlow

8% off
NZ$29,138
for 7 nights, 1 apartment
NZ$4,163 per night
includes taxes & fees
Mountain Paradise—SKI-ON/SKI-OFF Okemo Ski Getaway ⛷ hot tubs, pool, fireplace
Exterior
Interior
Dining
Private kitchen
Exceptional
(6 reviews)

Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!

Wilmington

7% off
NZ$13,741
for 7 nights, 1 home
NZ$1,963 per night
includes taxes & fees
Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
Kitchen and dining Area - seats 9 with bench / 2 at counter
Living area
Loft with surround sound Entertainment
Dining
Exceptional
(32 reviews)

Perfect Get-Away House - 6 Miles from Stratton & Mount Snow

West Wardsboro

5% off
NZ$11,176
for 7 nights, 1 home
NZ$1,597 per night
includes taxes & fees
Perfect Get-Away House - 6 Miles from Stratton & Mount Snow
Interior
Outdoor dining
Property grounds
Dining
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
NZ$7,384
for 7 nights, 1 home
NZ$1,055 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
View of dining/kitchen area from entrance landing.
View from deck.
Living area
Room
Exceptional
(25 reviews)

Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.

Wilmington

18% off
NZ$9,433
for 7 nights, 1 home
NZ$1,348 per night
includes taxes & fees
Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.
Dining
Living area
Room
Interior
Exceptional
(5 reviews)

Charming Home with Lake and Mountain View

Whitingham

8% off
NZ$16,925
for 7 nights, 1 cabin
NZ$2,418 per night
includes taxes & fees
Charming Home with Lake and Mountain View
Property grounds
Outdoor dining
Exterior
Living area
Exceptional
(31 reviews)

Secluded large country home for big groups with giant open yard for outdoor fun.

Whitingham

20% off
NZ$4,536
for 7 nights, 1 home
NZ$648 per night
includes taxes & fees
Secluded large country home for big groups with giant open yard for outdoor fun.
Screened in porch dining area
Property grounds
Exterior
Living Room
Exceptional
(21 reviews)

Cozy Vermont Home Near Mount Snow & Stratton

West Wardsboro

8% off
NZ$7,254
for 7 nights, 1 home
NZ$1,036 per night
includes taxes & fees
Cozy Vermont Home Near Mount Snow & Stratton
Exterior detail
Owner and guest parking. Private guest access is located through the porch door.
Hallway view from the bathroom looking toward the kitchen area.
Room
Exceptional
(35 reviews)

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

8% off
NZ$2,115
for 7 nights, 1 apartment
NZ$302 per night
includes taxes & fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Room
Private kitchen
Private kitchen
Living area
Exceptional
(19 reviews)

Cozy Condo Near MASS MoCA

North Adams

12% off
NZ$5,003
for 7 nights, 1 home
NZ$715 per night
includes taxes & fees
Cozy Condo Near MASS MoCA
Interior
Exterior
Interior
Interior
Exceptional
(73 reviews)

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!

Chester

8% off
NZ$3,506
for 7 nights, 1 cabin
NZ$501 per night
includes taxes & fees
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Welcome to Tallwood Timber VT
Large dining area accommodates family sized gatherings
Backyard - Fire Pit area
Living Room
Exceptional
(13 reviews)

Tallwood Timber: a Family Friendly Ski House in Southern Vermont

Londonderry

8% off
NZ$8,265
for 7 nights, 1 home
NZ$1,181 per night
includes taxes & fees
Tallwood Timber: a Family Friendly Ski House in Southern Vermont
Interior
Available weekend, weekly or monthly spring or summer rental.
Private kitchen
Interior
Exceptional
(32 reviews)

Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.

Jamaica

8% off
NZ$7,254
for 7 nights, 1 apartment
NZ$1,036 per night
includes taxes & fees
Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.
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    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:

  • Winhall River (9.5 mi / 15.3 km)
  • 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)

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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