Southern Vermont holiday rentals

We found 2,676 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southern Vermont

Showing deals for:25 Dec - 1 Jan

Room
Property grounds
Dining
Property grounds
Exceptional
(11 reviews)

the farmhouse at Big Picture Farm

Townshend

13% off
AU$30,230
for 7 nights, 1 room
AU$4,319 per night
includes taxes & fees
the farmhouse at Big Picture Farm
Exterior
Terrace/patio
Indoor hot tub
Two story living room with 70" smarttv, premium directtv and bluetooth turntable
Exceptional
(10 reviews)

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

Wilmington

17% off
AU$25,012
for 7 nights, 1 chalet
AU$3,573 per night
includes taxes & fees
HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake
Welcome to the Blue Moon Bungalow!
Fully stocked kitchen with plenty of room to prepare a family dinner
Bear Room - 2nd Floor bedroom with a king bed, tv with roku and sitting area.
The first floors open plan is great for large groups.
Exceptional
(11 reviews)

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

Chester

8% off
AU$6,366
for 7 nights, 1 chalet
AU$909 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?
Dining
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
AU$10,284
for 7 nights, 1 chalet
AU$1,469 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
Master 2 Second Floor
Exceptional
(101 reviews)

New Lakefront Log Home

Wilmington

12% off
AU$8,160
for 7 nights, 1 chalet
AU$1,166 per night
includes taxes & fees
New Lakefront Log Home
Fully equipped kitchen
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
AU$8,007
for 7 nights, 1 chalet
AU$1,144 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
AU$15,669
for 7 nights, 1 home
AU$2,238 per night
includes taxes & fees
Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY
Dining area
Large open-concept living and kitchen area
Bedroom 1: Queen Bed
3-Season porch (new addition 2023)
Exceptional
(18 reviews)

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

Wardsboro

8% off
AU$14,690
for 7 nights, 1 cabin
AU$2,099 per night
includes taxes & fees
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Dining
Terrace/patio
Private kitchen
Room
Exceptional
(20 reviews)

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

Williamstown

16% off
AU$4,379
for 7 nights, 1 cottage
AU$626 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Private kitchen
Property grounds
Living area
Exterior
Exceptional
(28 reviews)

Bear Pass Bunkhouse

Manchester

8% off
AU$3,124
for 7 nights, 1 home
AU$446 per night
includes taxes & fees
Bear Pass Bunkhouse
Private driveway with ramp to enter house. Gently babbling stream in the front
Front of house, early spring
Light filled kitchen
Open living room with french doors, huge windows & vaulted ceiling
Exceptional
(7 reviews)

Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible

Weston

8% off
AU$5,983
for 7 nights, 1 home
AU$855 per night
includes taxes & fees
Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible
Living area
Pool in the nearby recreational building
Room
Dining
Exceptional
(140 reviews)

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

Ludlow

8% off
AU$23,382
for 7 nights, 1 apartment
AU$3,340 per night
includes taxes & fees
Mountain Paradise—SKI-ON/SKI-OFF Okemo Ski Getaway ⛷ hot tubs, pool, fireplace
Exterior
Interior
Private kitchen
Living area
Exceptional
(6 reviews)

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

Wilmington

8% off
AU$10,634
for 7 nights, 1 home
AU$1,519 per night
includes taxes & fees
Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
Loft with surround sound Entertainment
Living area
Kitchen and dining Area - seats 9 with bench / 2 at counter
Dining
Exceptional
(32 reviews)

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

West Wardsboro

5% off
AU$8,882
for 7 nights, 1 home
AU$1,269 per night
includes taxes & fees
Perfect Get-Away House - 6 Miles from Stratton & Mount Snow
Property grounds
Outdoor dining
Dining
Renovated kitchen
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
AU$5,883
for 7 nights, 1 home
AU$840 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Room
Living area
Outdoor dining
Interior
Exceptional
(5 reviews)

Charming Home with Lake and Mountain View

Whitingham

8% off
AU$13,706
for 7 nights, 1 cabin
AU$1,958 per night
includes taxes & fees
Charming Home with Lake and Mountain View
Room
View from deck.
Living area
View of dining/kitchen area from entrance landing.
Exceptional
(25 reviews)

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

Wilmington

18% off
AU$7,487
for 7 nights, 1 home
AU$1,070 per night
includes taxes & fees
Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.
Property grounds
Outdoor dining
Living area
Living area
Exceptional
(31 reviews)

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

Whitingham

20% off
AU$3,648
for 7 nights, 1 home
AU$521 per night
includes taxes & fees
Secluded large country home for big groups with giant open yard for outdoor fun.
Private kitchen
Property grounds
Screened in porch dining area
Exterior
Exceptional
(21 reviews)

Cozy Vermont Home Near Mount Snow & Stratton

West Wardsboro

8% off
AU$5,776
for 7 nights, 1 home
AU$825 per night
includes taxes & fees
Cozy Vermont Home Near Mount Snow & Stratton
Hallway view from the bathroom looking toward the kitchen area.
Owner and guest parking. Private guest access is located through the porch door.
Exterior detail
A small kitchenette fully equipped for small-scale cooking.
Exceptional
(35 reviews)

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

8% off
AU$1,700
for 7 nights, 1 apartment
AU$243 per night
includes taxes & fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Private kitchen
Private kitchen
Interior
Room
Exceptional
(19 reviews)

Cozy Condo Near MASS MoCA

North Adams

12% off
AU$3,948
for 7 nights, 1 home
AU$564 per night
includes taxes & fees
Cozy Condo Near MASS MoCA
Interior
Exterior
Interior
Terrace/patio
Exceptional
(73 reviews)

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

Chester

8% off
AU$2,845
for 7 nights, 1 cabin
AU$406 per night
includes taxes & fees
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Backyard - Fire Pit area
Large dining area accommodates family sized gatherings
Living Room
Wood burning stove 1
Exceptional
(13 reviews)

Tallwood Timber: a Family Friendly Ski House in Southern Vermont

Londonderry

8% off
AU$6,602
for 7 nights, 1 home
AU$943 per night
includes taxes & fees
Tallwood Timber: a Family Friendly Ski House in Southern Vermont
Private kitchen
Available weekend, weekly or monthly spring or summer rental.
Interior
Outdoor dining
Exceptional
(32 reviews)

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

Jamaica

8% off
AU$5,776
for 7 nights, 1 apartment
AU$825 per night
includes taxes & fees
Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.
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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. Stayz 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 Stayz 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, Stayz 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 Stayz 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 Stayz, 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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