Location

Dates

Guests

Vacation rentals in Poultney, Vermont, United States

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

Looking back up at the house with the lake behind you.

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

View of the house and garage as you turn into the driveway from the private road leading up to our home.

View from across Little Lake

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

3 bedrooms·3½ baths

Wells • Vermont

4.98(95 reviews)

$1,387.00 USD total for 3 nights

Sep 28 – Oct 1, 2026

Free cancellation

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)

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

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

Carriage House

2 bedrooms·2 baths

Mount Holly • Vermont

$927.00 USD total for 3 nights

Sep 7 – 10, 2026

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)

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

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

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 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

Manchester Sanctuary escape to Vermont!

Manchester Sanctuary escape to Vermont!

Manchester Sanctuary escape to Vermont!

Manchester Sanctuary escape to Vermont!

Manchester Sanctuary escape to Vermont!

Manchester Sanctuary escape to Vermont!

3 bedrooms·3½ baths

Manchester • Vermont

5(2 reviews)

$1,756.00 USD total for 3 nights

Sep 30 – Oct 3, 2026

Free cancellation

the view of the front of the home with the wrap around deck!

This is the view of the rear of the home

the access ramp

entry to the home at the rear.

Enter via the mudroom and please remove your shoes!

Manchester Santuary II

4 bedrooms·4½ baths

Manchester • Vermont

5(1 review)

$1,925.50 USD total for 3 nights

Sep 7 – 10, 2026

Renovated 2BR on Bromley | Fall Foliage & Hiking

Renovated 2BR on Bromley | Fall Foliage & Hiking

Renovated 2BR on Bromley | Fall Foliage & Hiking

Renovated 2BR on Bromley | Fall Foliage & Hiking

Renovated 2BR on Bromley | Fall Foliage & Hiking

Renovated 2BR on Bromley | Fall Foliage & Hiking

2 bedrooms·1 bath

Peru • Vermont

4.61(28 reviews)

$839.45 USD total for 3 nights

Sep 7 – 10, 2026

Cozy Bromley Retreat

Cozy Bromley Retreat

Cozy Bromley Retreat

Cozy Bromley Retreat

Cozy Bromley Retreat

Cozy Bromley Retreat

1 bedroom·1 bath

Peru • Vermont

5(1 review)

$546.13 USD total for 3 nights

Sep 7 – 10, 2026

Enjoy casual conversations in this cozy living room that is flooded with natural light during the day.

High speed internet available for quick connections and streaming video.

The house is a custom timber frame with distinct and timeless styling that blends into the surrounding area.

Newly added washer and dryer for quick cleanups or drying skiing gear.

Star gazing at night is a perfect way to unwind and enjoy the seclusion.

Tranquil Brookside Retreat with Hot Tub & Firepit

4 bedrooms·2½ baths

Peru • Vermont

5(1 review)

$1,137.44 USD total for 3 nights

Sep 7 – 10, 2026

Shadow Peak Chalet

Shadow Peak Chalet

Shadow Peak Chalet

Shadow Peak Chalet

Shadow Peak Chalet

Shadow Peak Chalet

4 bedrooms·2 baths

Manchester • Vermont

$1,076.15 USD total for 3 nights

Sep 13 – 16, 2026

The Little Matterhorn

The Little Matterhorn

The Little Matterhorn

The Little Matterhorn

The Little Matterhorn

The Little Matterhorn

3 bedrooms·2 baths

Winhall • Vermont

4.87(30 reviews)

$934.30 USD total for 3 nights

Sep 8 – 11, 2026

Enjoy a movie and some theater style popcorn in our living room and open kitchen

Jacuzzi Hot Tub

The kitchen is stocked with everything you need to wow your family and friends with your culinary abilities, or just keep the drinks cold and go out, all Weston has to offer is mere footsteps

Challenge each other to a game of basketball, arcade classic Mortal Kombat 3 or one of many others - while the rest of the crew catches a flick waiting for their turn to play.

Feel the warmth of 200 year old post and beam construction

The Historic Rideout

6 bedrooms·6 baths

Weston • Vermont

4.92(36 reviews)

$1,745.18 USD $1,507.29 USD total for 3 nights

Sep 7 – 10, 2026

Enjoy a crackling fire in our living room and open kitchen

Jacuzzi Tub Added July '23

The kitchen is stocked with everything you need to wow your family and friends with your culinary abilities, or just keep the drinks cold and go out, all Weston has to offer is mere footsteps

Challenge each other to a game of basketball, arcade classic mortal kombat 2 (or one of many others) - while the rest of the crew catches a flick waiting for their turn to play.

Feel the warmth of 200 year old post and beam construction

The Historic Rideout

6 bedrooms·6 baths

Weston • Vermont

$2,572.72 USD total for 3 nights

Sep 7 – 10, 2026

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

4 bedrooms·5 baths

Winhall • Vermont

5(8 reviews)

$1,042.94 USD total for 3 nights

Sep 7 – 10, 2026

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

4 bedrooms·2 baths

Winhall • Vermont

5(10 reviews)

$912.00 USD total for 3 nights

Sep 7 – 10, 2026

Casita Bacon

4 bedrooms·4 baths

Winhall • Vermont

$1,132.06 USD total for 3 nights

Sep 7 – 10, 2026

Relax by the fire in our 8 leather recliners & 3 bean bag chairs

Eat Breakfast by the Pellet Stove & Feel the vibes of 1830s Post & Beam Construction

Our Expansive Chef's Kitchen

Have yourself a steam in our Sauna

Red Brick Retreat

8 bedrooms·6 baths

Londonderry • Vermont

5(24 reviews)

$3,565.96 USD $3,274.27 USD total for 3 nights

Sep 11 – 14, 2026