Location

Dates

Guests

Vacation rentals in Brandon, Vermont, United States

Front of the home from the two-car off street parking pad. Walkway lights up at night for later check-ins.

Cute, Renovated Home on River, Walk to Downtown

Cute, Renovated Home on River, Walk to Downtown

Spacious upstairs full bath

Cute, Renovated Home on River, Walk to Downtown

Cute, Renovated Home on River, Walk to Downtown

3 bedrooms·1½ baths

Brandon • Vermont

4.8(51 reviews)

$788.00 USD total for 3 nights

Sep 14 – 17, 2026

Wrap Around Deck

Killington Grandview House

7 bedrooms·6½ baths

Mendon • Vermont

4.86(7 reviews)

$4,027.55 USD total for 3 nights

Sep 7 – 10, 2026

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

4 bedrooms·3 baths

Rutland • Vermont

5(10 reviews)

$406 – $2,670/ night(excl. fees & taxes)

Epic Farm, House, Barn image 1

Epic Farm, House, Barn image 2

Dog not included

Epic Farm, House, Barn image 4

Epic Farm, House, Barn image 5

Epic House, Barn, Farm

11 bedrooms·3½ baths

Rochester • Vermont

4.9(29 reviews)

$791/ night(excl. fees & taxes)

View of the house from the driveway. On over an acre, surrounded by trees.

View of the house as you head up the driveway. House sits on an acre+ lot.

Kitchen with space for two at the counter.

Upgraded kitchen with quartz counters and stainless steel appliances.

Dining room & kitchen combo opens to the living room too for easy conversation.

The Crooked House

3 bedrooms·2½ baths

Stockbridge • Vermont

5(100 reviews)

$971.00 USD total for 3 nights

Sep 7 – 10, 2026

Heavenly Killington 16 ppl, 7 bedrooms, 4 bathrooms, 11 beds. Free parking for 10+ cars. Tesla charger.

Heavenly Killington 16 ppl, 7 bedrooms, 4 bathrooms, 11 beds. Free parking for 10+ cars. Tesla charger.

House front view

Unit 1 Great room

Unit 1 Great room

Heavenly Killington

7 bedrooms·4 baths

Killington • Vermont

5(83 reviews)

$2,838.56 USD $2,611.21 USD total for 3 nights

Sep 7 – 10, 2026

Living room is equipped with large handmade Chesterfield leather sofa, two vintage leather club chairs and vintage leather recliner. An exceptionally large wood-burning fireplace flanked by antique ski equipment adds warmth for cold Vermont nights.

Living room with large handmade Chesterfield leather sofa, two vintage leather club chairs and vintage leather recliner chair is perfect for snuggling up in front of fire with a good book, or binging on a new Netflix series.

The open plan living and dining room with 8 seat table and antique handmade ski light fixture make Kilbourne Lodge a perfect place to both entertain and relax.

Present day Kilbourne Lodge. A mid-century angled roof ski chalet with large accent stone wall. Front deck features a vintage 2-seater ski lift chair painted in bright red. 100% Instagram worthy!

King bed with memory foam mattress, individual reading lights and ski-shoe side-tables.

Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer

3 bedrooms·2 baths

Killington • Vermont

4.91(33 reviews)

$1,248.80 USD total for 3 nights

Sep 7 – 10, 2026

Cozy, clean, and bright open-concept living room & kitchen

Mountain view on the deck off the living room

Desk converts to dining table for 4

Unwind with a quiet & serene view of the slopes

Remote work-friendly desk, workspace, high-speed internet

Killington VT Condo - Mountain Green

1 bedroom·1 bath

Killington • Vermont

$1,666.24 USD total for 3 nights

Nov 24 – 27, 2026

Free cancellation

Back yard wild flowers

Dock and storage shed for kayaks and fire pit chairs

Hot tub with outdoor shower

The house is at the top of the photo. The backyard is 1.5 acres with a path leading to the lake, dock, and fire pit

Serenity Now !

2 bedrooms·3 baths

Bridport • Vermont

$425/ night(excl. fees & taxes)

Exterior view of House. Stairs from Driveway and Deck.

Dining Room with chairs for 8

Dining Room. Sliding door with access to east deck & gas Grill

Fully equipped kitchen. New stainless steel look appliances

Leather sofa and love seat

Private House with Fantastic Views off Home Stretch Trail

4 bedrooms·2 baths

Killington • Vermont

5(48 reviews)

$2,750.00 USD total for 4 nights

Sep 7 – 11, 2026

Living room 2 - this space can be bright and open, or close the shades on the skylights and have a cozy, warm nook.

Bedroom 3 - the sunroom. Surrounded by windows with a door leading to the covered porch w/ swing and a bistro table. Perfect for catching sunrise! A second door leads to a private woodland garden.

Sitting window found in Bedroom 1 (Large Loft). Views of backyard, fire pit, and perennial gardens.

Kismet Cabin: Ski Sugarbush & Summer Lake Days

3 bedrooms·2 baths

Warren • Vermont

5(32 reviews)

$2,308.31 USD total for 3 nights

Oct 10 – 13, 2026

Free cancellation

Handcrafted VT Chalet • Walk to Lake • Fire Pit image 1

Spacious open floor plan with fireplace, vaulted ceilings and natural light.

Handcrafted VT Chalet • Walk to Lake • Fire Pit image 3

Handcrafted VT Chalet • Walk to Lake • Fire Pit image 4

Full bathroom with all the amenities.

Handcrafted Log Chalet (sleeps 2-4)

1 bedroom·1 bath

Warren • Vermont

$1,160.71 USD total for 3 nights

Oct 10 – 13, 2026

Free cancellation

Private entrance with a spacious deck nestled high among the trees—perfect for savoring your morning coffee, soaking in the fresh Vermont air, or enjoying the peaceful silence.

Open living room and kitchen area. 40' smart TV, full size pull out sofa bed, 2 bar stools at kitchen counter for dining.
Door leads to 2nd story deck & stairs (summer entrance).
Interior stairs are the winter entrance through garage.

Queen bedroom with a plush new mattress topper and soft, cozy bedding.

Bright, clean bathroom stocked with all the essentials—plus a little extra to make your stay more comfortable!

Whether you're playing lawn games, reading beneath the trees, or simply stretching out in an Adirondack chair, there's room to enjoy Vermont at your own pace.

Alpine Apartment Suite

1 bedroom·1 bath

Warren • Vermont

5(51 reviews)

$729.35 USD total for 3 nights

Sep 11 – 14, 2026

Lake Saint Catherine Cottage with Private Dock

Lake Saint Catherine Cottage with Private Dock

Lake Saint Catherine Cottage with Private Dock

Lake Saint Catherine Cottage with Private Dock

Lake Saint Catherine Cottage with Private Dock

Lake Saint Catherine Cottage with Private Dock

2 bedrooms·2 baths

Poultney • Vermont

$1,488.21 USD total for 3 nights

Sep 7 – 10, 2026

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

4 bedrooms·3½ baths

Plymouth • Vermont

$1,497.62 USD total for 3 nights

Oct 27 – 30, 2026

Free cancellation

Mount Holly Lake & Ski Hideaway

Mount Holly Lake & Ski Hideaway

Mount Holly Lake & Ski Hideaway

Fall in Mount Holly

Mount Holly Lake & Ski Hideaway

Mount Holly Lake & Ski Hideaway

4 bedrooms·2 baths

Mount Holly • Vermont

5(37 reviews)

$299/ night(excl. fees & taxes)

Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape

Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape

Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape

Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape

Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape

Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape

3 bedrooms·1 bath

Brookfield • Vermont

4.88(16 reviews)

$685.00 USD total for 3 nights

Sep 7 – 10, 2026

Carriage House

2 bedrooms·2 baths

Mount Holly • Vermont

$927.00 USD total for 3 nights

Sep 7 – 10, 2026

1930s-era cottage.

Private outdoor hot tub under cover.

Outdoor fire pit

Primary bedroom with king bed. Featuring a Puffy mattress, fine linens, plenty of pillows, and a down comforter.

The living room opens up to a larger screened-in porch. Dining also on the porch. It features a wood-burning fireplace for cooler times. It will be all set to light and we provide plenty of wood.

Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs

1 bedroom·2 baths

Plymouth • Vermont

$1,191.00 USD total for 3 nights

Sep 7 – 10, 2026

Get-Away Cabin in Plymouth, Vermont.

Aerial view of Lake Amherst

Large screened-in porch overlooking the lake.

Get-Away Cabin in Plymouth, Vermont.

Get-Away Cabin in Plymouth, Vermont.

1 bedroom·2 baths

Plymouth • Vermont

5(34 reviews)

$1,107.00 USD total for 3 nights

Sep 7 – 10, 2026

We are currently updating our photos.
Front lawn view

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

6 bedrooms·4 baths

Plymouth • Vermont

4.98(90 reviews)

$6,582.00 USD total for 6 nights

Sep 15 – 21, 2026

Twilight ~ CURRENTLY UPDATING PICTURES ~ STAY TUNED!

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

4 bedrooms·3 baths

Plymouth • Vermont

5(55 reviews)

$2,294.20 USD total for 3 nights

Sep 7 – 10, 2026

The front porch at dusk

Cute Cabin! Plymouth, Vermont.

Cute Cabin! Plymouth, Vermont.

Cute Cabin! Plymouth, Vermont.

Cute Cabin! Plymouth, Vermont.

3 bedrooms·3 baths

Plymouth • Vermont

5(52 reviews)

$2,031.00 USD total for 3 nights

Sep 8 – 11, 2026

NirvanaSanctuaryHouse~Fire Place~Okemo Killington

NirvanaSanctuaryHouse~Fire Place~Okemo Killington

Hot Tub Area
Undercover!

Hot Springs Hot Tub ~ seats 4

King Master Bedroom

NirvanaSanctuaryHouse~Fire Place~Okemo Killington

2 bedrooms·3 baths

Plymouth • Vermont

5(31 reviews)

$1,695.00 USD total for 3 nights

Sep 8 – 11, 2026