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Holiday homes in Stockbridge

Enjoy your stay and find the best Holiday homes in Stockbridge at affordable prices

Searching for a holiday home in Stockbridge (Vermont)? Explore a great selection of vacation homes in Stockbridge to find the one that best fits to your needs, starting from $120 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Stockbridge and region (30 miles)
Killington Area Escape with Deck, Views and Hot Tub! in Stockbridge, USA

Killington Area Escape with Deck, Views...

Holiday home in Stockbridge, Vermont
Located in Stockbridge, 23 km from Killington Mountain, 15 km from Gifford Woods State Park and 18 km from Pico Peak, Killington Area Escape with Deck...
  • Parking

no reviews

from $372.00 Show details »

Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes in Pittsfield, USA

Silver Spring Chalet Large 4 bedroom, Pi...

Holiday home in Pittsfield near Stockbridge, Vermont , 102 Silver Spring Hill Road City
Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes is located in Pittsfield, 23 km from Killington Mountain and 14 km fr...
  • Pets allowed
  • Fitness centre
  • Tea/Coffee maker
  • Shower
  • Refrigerator

no reviews

from $300.00 Show details »

Wintergreen 106 - Cozy and peaceful condo, conveniently located between Killington and Pittsfield in Pittsfield, USA

Wintergreen 106 - Cozy and peaceful cond...

Holiday home in Pittsfield near Stockbridge, Vermont , 2358 Rt. 100 North
Wintergreen 106 - Cozy and peaceful condo, conveniently located between Killington and Pittsfield is set in Pittsfield, 21 km from Killington Mountain...

no reviews

from $120.00 Show details »

Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington in Pittsfield, USA

Sweet Life - Vermont Chalet - 6 person I...

Holiday home in Pittsfield near Stockbridge, Vermont , Dove Drive
Located in Pittsfield, this villa is 10 km from Killington.
  • Pets allowed
  • Spa and wellness centre
  • Tea/Coffee maker
  • Shower
  • Bath

Exceptional 1 Reviews 10.0

from $252.00 Show details »

Perfect secluded 3 bedroom cozy getaway home Hawk Landing in Pittsfield, USA

Perfect secluded 3 bedroom cozy getaway...

Holiday home in Pittsfield near Stockbridge, Vermont , 132 Hawk Ln
Hawk Landing offers accommodation in Pittsfield.
  • Parking

no reviews

from $322.00 Show details »

Pittsfield Paradise in Pittsfield, USA

Pittsfield Paradise

Holiday home in Pittsfield near Stockbridge, Vermont
Set in Pittsfield, 23 km from Killington Mountain, Pittsfield Paradise offers accommodation with a garden, free WiFi and an ATM.
  • Parking

Exceptional 1 Reviews 10.0

from $382.55 Show details »

Vermont Retreat - 8 Mi to Killington Ski Area in Killington, USA

Vermont Retreat - 8 Mi to Killington Ski...

Holiday home in Killington near Stockbridge, Vermont
Located 4 km from Gifford Woods State Park, 7.4 km from Pico Peak and 39 km from Mount Tom, Vermont Retreat - 8 Mi to Killington Ski Area provides acc...
  • Parking

Very good 2 Reviews 8.5

from $236.00 Show details »

Cricket Hill in Killington, USA

Cricket Hill

Holiday home in Killington near Stockbridge, Vermont , 414 Cricket Hill Road
Cricket Hill is situated in Killington.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 26 Reviews 9.0

from $235.00 Show details »

Bob's Bungalow in North Sherburne, USA

Bob's Bungalow

Holiday home in North Sherburne near Stockbridge, Vermont
Set in Killington, Bobs Bungalow features accommodation with a TV and a kitchen.
  • Parking
  • Pets allowed
  • Tea/Coffee maker
  • Shower
  • Bath

Very good 2 Reviews 8.5

from $132.33 Show details »

Rustic 3 bedroom home Moose Lodge in Killington, USA

Rustic 3 bedroom home Moose Lodge

Holiday home in Killington near Stockbridge, Vermont , 589 Barrows Towne Road
The perfect ski house!
  • Parking

no reviews

from $374.33 Show details »

Sunrise Village in Killington, USA

Sunrise Village

Holiday home in Killington near Stockbridge, Vermont
Sunrise Village offers accommodation in Killington.
  • Parking
  • Fitness centre
  • Indoor pool
  • Outdoor pool
  • Swimming pool

no reviews

from $216.50 Show details »

1795 Farmhouse in Barnard, USA

1795 Farmhouse

Holiday home in Barnard near Stockbridge, Vermont
Boasting garden views, 1795 Farmhouse features accommodation with a patio and a coffee machine, around 48 km from Killington Mountain.
  • Parking

no reviews

from $412.67 Show details »

Woods Village 34 in Killington, USA

Woods Village 34

Holiday home in Killington near Stockbridge, Vermont , 34 Village Circle
Woods Village 34, a property with a terrace, is set in Killington, 8.5 km from Killington Mountain, 200 metres from Gifford Woods State Park, as well ...
  • Parking
  • Indoor pool
  • Swimming pool
  • Swimming Pool
  • Tea/Coffee maker

Very good 1 Reviews 8.0

from $145.88 Show details »

Spacious Townhouse Great for large groups family Snow Flake in Killington, USA

Spacious Townhouse Great for large group...

Holiday home in Killington near Stockbridge, Vermont , 162 Spring Hill Road
Snow Flake is situated in Killington, 3.8 km from Gifford Woods State Park and 5.2 km from Pico Peak, in an area where skiing can be enjoyed.
  • Parking
  • Shower
  • Bath
  • Iron
  • Refrigerator

no reviews

from $305.33 Show details »

Spacious Townhouse Great for large groups family Snow Flurry in Killington, USA

Spacious Townhouse Great for large group...

Holiday home in Killington near Stockbridge, Vermont , 162 Spring Hill Road
Snow Flurry is situated in Killington, 3.8 km from Gifford Woods State Park and 5.2 km from Pico Peak, in an area where skiing can be enjoyed.
  • Parking
  • Shower
  • Bath
  • Iron
  • Refrigerator

no reviews

from $213.57 Show details »

Quaint Condo 5 minutes to the ski slopes Valley Park D1 in Killington, USA

Quaint Condo 5 minutes to the ski slopes...

Holiday home in Killington near Stockbridge, Vermont , 140 Valley Park Circle
Valley Park D1 is located in Killington, 8.4 km from Killington Mountain and 5 km from Gifford Woods State Park, in an area where skiing can be enjoye...
  • Shower
  • Bath
  • Refrigerator
  • Toilet
  • Microwave

Exceptional 3 Reviews 9.7

from $236.07 Show details »

Breakaway House by Killington Vacation Rentals in Killington, USA

Breakaway House by Killington Vacation R...

Holiday home in Killington near Stockbridge, Vermont
Located 6.1 km from Killington Mountain, Breakaway House by Killington Vacation Rentals offers a garden, and air-conditioned accommodation with a pati...
  • Parking
  • Pets allowed

no reviews

from $404.10 Show details »

Woods Village 37 in Killington, USA

Woods Village 37

Holiday home in Killington near Stockbridge, Vermont , 166 Village Circle
Woods Village 37, a property with a terrace, is set in Killington, 6.9 km from Killington Mountain, 3.5 km from Gifford Woods State Park, as well as 4...
  • Parking
  • Indoor pool
  • Swimming pool
  • Swimming Pool
  • Tea/Coffee maker

Fabulous 1 Reviews 9.0

from $126.00 Show details »

Your Ski Home- Powder Park Place - Lower Level, Close to Killington, home in Killington, USA

Your Ski Home- Powder Park Place - Lower...

Holiday home in Killington near Stockbridge, Vermont
Your Ski Home- Powder Park Place - Lower Level, Close to Killington, home in Killington features accommodation with free WiFi, 6.7 km from Killington ...
  • Parking
  • Pets allowed
  • Electric vehicle charging station

no reviews

from $303.48 Show details »

Woods Resort and Spa Village 9 in Killington, USA

Woods Resort and Spa Village 9

Holiday home in Killington near Stockbridge, Vermont , 119 Village Circle
Situated in Killington, 6.9 km from Killington Mountain, 3.4 km from Gifford Woods State Park and 4.8 km from Pico Peak, Woods Resort and Spa Village ...
  • Parking
  • Spa and wellness centre
  • Indoor pool
  • Swimming pool
  • Swimming Pool

Very good 1 Reviews 8.0

from $292.00 Show details »

Condos at The Woods Resort Resort and Spa in Killington, USA

Condos at The Woods Resort Resort and Sp...

Holiday home in Killington near Stockbridge, Vermont , 53 Woods Lane
Set within 6.2 km of Killington Mountain and 2.7 km of Gifford Woods State Park in Killington, Condos at The Woods Resort Resort and Spa offers accomm...
  • Sauna
  • Fitness centre
  • Spa and wellness centre
  • Tea/Coffee maker
  • Shower

no reviews

from $147.60 Show details »

Beautiful condo with fireplace, on site spa & fitness center Woods Resort 26 in Killington, USA

Beautiful condo with fireplace, on site...

Holiday home in Killington near Stockbridge, Vermont , 185 Woods Road
Woods Resort Unit V26 is situated in Killington, 4.3 km from Killington Resort.
  • Parking
  • Indoor pool
  • Swimming pool
  • Swimming Pool
  • Bath

Superb 5 Reviews 9.2

from $290.40 Show details »

Just a stone's throw from the heart of town, this 2 bedrooms unit features a whirlpool tub, fireplace and sport center in Killington, USA

Just a stone's throw from the heart of t...

Holiday home in Killington near Stockbridge, Vermont , 229 Village Circle
Located 6.2 km from Killington Mountain, 2.8 km from Gifford Woods State Park and 4.1 km from Pico Peak, Woods Resort Unit V17 provides accommodation ...
  • Parking
  • Indoor pool
  • Swimming pool
  • Swimming Pool
  • Shower

Fabulous 6 Reviews 8.8

from $282.07 Show details »

The Woods: Village-11 in Killington, USA

The Woods: Village-11

Holiday home in Killington near Stockbridge, Vermont
The Woods: Village-11 is set in Killington, 4.4 km from Killington Resort.
  • Parking
  • Sauna
  • Fitness centre
  • Outdoor pool
  • Swimming pool

Very good 25 Reviews 8.2

from $263.84 Show details »

The Tanglewood Lodge- Amazing Ski Home for Groups, Hot Tub, Close to Killington Resort! home in Killington, USA

The Tanglewood Lodge- Amazing Ski Home f...

Holiday home in Killington near Stockbridge, Vermont , 694 Tanglewood Dr
The Tanglewood Lodge- Amazing Ski Home for Groups, Hot Tub, Close to Killington Resort! home is set in Killington, 6.8 km from Killington Mountain, an...
  • Parking
  • Pets allowed

no reviews

from $393.88 Show details »

Number of Holiday homes in Stockbridge 224
Average price per night $396.03
Lowest price per night $120.00
Highest price per night $1.910.43

Most popular Holiday-homes in Stockbridge

The most popular Holiday-homes in Stockbridge based on average guest rating (Top 10).

Cheapest Holiday-homes in Stockbridge

The cheapest Holiday-homes in Stockbridge based on room rate per night (Top 10).

Most booked Holiday-homes in Stockbridge

The most booked Holiday-homes in Stockbridge based on popularity with guests (Top 10).

Holiday homes in Stockbridge (Vermont), comfortable and familiar

Staying in a holiday or vacation home in Stockbridge can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Stockbridge for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Stockbridge should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com