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Holiday homes in Chesterfield

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

Searching for a holiday home in Chesterfield (New Hampshire)? Explore a great selection of vacation homes in Chesterfield to find the one that best fits to your needs, starting from $108 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Chesterfield and region (40 miles)
Newfane Hill Retreat in Newfane, USA

Newfane Hill Retreat

Holiday home in Newfane near Chesterfield, New Hampshire
Set in Newfane, 41 km from Stratton Mountain, 21 km from Fort Dummer State Park and 23 km from Mount Snow Resort, Newfane Hill Retreat offers accommod...
  • Parking
  • Pets allowed
  • Sauna

Passable 2 Reviews 5.0

from $197.00 Show details »

Timeless Red Sox Retreat with Scenic Mountain Views! in Putney, USA

Timeless Red Sox Retreat with Scenic Mou...

Holiday home in Putney near Chesterfield, New Hampshire
Situated in Putney, 7.2 km from Santa s Land, 13 km from Bellows Falls Amtrak Station and 35 km from Fort Dummer State Park, Timeless Red Sox Retreat ...
  • Parking
  • Sauna
  • Internet facilities
  • Iron
  • Refrigerator

no reviews

from $458.67 Show details »

Cozy Fiddlers Rest Cabin 11 Miles to Skiing! in Bernardston, USA

Cozy Fiddlers Rest Cabin 11 Miles to Ski...

Holiday home in Bernardston near Chesterfield, New Hampshire
Cozy Fiddlers Rest Cabin 11 Miles to Skiing! is situated in Bernardston, 49 km from Amherst College and 50 km from Pratt Museum of Natural History, in...
  • Parking
  • Pets allowed

no reviews

from $266.00 Show details »

Rustic-Chic Cottage with Yard and Grill - Near Hiking! in Northfield, USA

Rustic-Chic Cottage with Yard and Grill...

Holiday home in Northfield near Chesterfield, New Hampshire
Located in Northfield, 39 km from Amherst College and 39 km from Pratt Museum of Natural History, Rustic-Chic Cottage with Yard and Grill - Near Hikin...
  • Parking

Superb 21 Reviews 9.4

from $210.00 Show details »

Mandy's Mountain Chalet in Dover, USA

Mandy's Mountain Chalet

Holiday home in Dover near Chesterfield, New Hampshire , 15 Mandys Road
Set in Dover, 38 km from Stratton Mountain, Mandys Mountain Chalet offers accommodation with a shared lounge, free WiFi and a shared kitchen.
  • Parking
  • Family rooms

no reviews

from $246.87 Show details »

Wilmington Home on 18 Acres about 9 Mi to Skiing! in Wilmington, USA

Wilmington Home on 18 Acres about 9 Mi t...

Holiday home in Wilmington near Chesterfield, New Hampshire
Wilmington Home on 18 Acres about 9 Mi to Skiing! is situated in Wilmington, 46 km from Bennington Battle Monument, 44 km from Bennington Museum, and ...
  • Parking
  • Pets allowed

no reviews

from $347.67 Show details »

Whites Hill Ski Retreat in Dover, USA

Whites Hill Ski Retreat

Holiday home in Dover near Chesterfield, New Hampshire
Located in Dover, 39 km from Stratton Mountain, Whites Hill Ski Retreat provides accommodation with a garden, free WiFi and an ATM.
  • Parking

Good 9 Reviews 7.6

from $248.93 Show details »

Dover Home 7 Mi to Mount Snow Grand Summit Resort in Dover, USA

Dover Home 7 Mi to Mount Snow Grand Summ...

Holiday home in Dover near Chesterfield, New Hampshire
Featuring a spa bath, Dover Home 7 Mi to Mount Snow Grand Summit Resort is located in Dover.
  • Parking
  • Internet facilities
  • Hairdryer
  • Spa bath
  • Refrigerator

no reviews

from $412.00 Show details »

Charming Wilmington Cabin, 8 Mi to Mt Snow! in Wilmington, USA

Charming Wilmington Cabin, 8 Mi to Mt Sn...

Holiday home in Wilmington near Chesterfield, New Hampshire
Situated 42 km from Bennington Battle Monument, 40 km from Bennington Museum and 42 km from Southern Vermont College, Charming Wilmington Cabin, 8 Mi ...
  • Parking
  • Hairdryer
  • Iron
  • Refrigerator
  • Toilet

Very good 1 Reviews 8.0

from $147.67 Show details »

Jacksonville Cabin with Wraparound Deck and Views in Jacksonville, USA

Jacksonville Cabin with Wraparound Deck...

Holiday home in Jacksonville near Chesterfield, New Hampshire
Situated 46 km from Bennington Battle Monument, 49 km from Stratton Mountain and 44 km from Bennington Museum, Jacksonville Cabin with Wraparound Deck...
  • Parking
  • Internet facilities
  • Shower
  • Bath
  • TV

Exceptional 2 Reviews 10.0

from $265.00 Show details »

Log Cabin Escape in Jacksonville, USA

Log Cabin Escape

Holiday home in Jacksonville near Chesterfield, New Hampshire
Offering mountain views, Log Cabin Escape is an accommodation located in Jacksonville, 46 km from Bennington Museum and 48 km from Southern Vermont Co...
  • Parking
  • Tea/Coffee maker
  • Internet facilities
  • Shower
  • Bath

Good 8 Reviews 7.5

from $223.25 Show details »

Wilmington Escape in Wilmington, USA

Wilmington Escape

Holiday home in Wilmington near Chesterfield, New Hampshire
Situated in Wilmington, 41 km from Bennington Battle Monument, Wilmington Escape features accommodation with a garden, free WiFi and an ATM.
  • Parking
  • Pets allowed
  • Tea/Coffee maker
  • Shower
  • Bath

Very good 3 Reviews 8.0

from $323.00 Show details »

Warm and Inviting Jamaica Cabin with Grill Ski and Hike in Jamaica, USA

Warm and Inviting Jamaica Cabin with Gri...

Holiday home in Jamaica near Chesterfield, New Hampshire
Warm and Inviting Jamaica Cabin with Grill Ski and Hike is situated in Jamaica, 21 km from Stratton Mountain, 39 km from Mount Equinox, as well as 28 ...
  • Parking
  • Internet facilities
  • Hairdryer
  • Fan
  • Toilet

no reviews

from $231.00 Show details »

Vermont Getaway with Deck - 6 Miles to Mt Snow! in Wilmington, USA

Vermont Getaway with Deck - 6 Miles to M...

Holiday home in Wilmington near Chesterfield, New Hampshire
Vermont Getaway with Deck - 6 Miles to Mt Snow! is situated in Wilmington, 36 km from Stratton Mountain, 42 km from Bennington Battle Monument, as wel...
  • Parking
  • Pets allowed
  • Shower
  • Bath
  • TV

no reviews

from $383.00 Show details »

Wooded Wonder in West Dover, USA

Wooded Wonder

Holiday home in West Dover near Chesterfield, New Hampshire
Situated in West Dover, 34 km from Stratton Mountain, 50 km from Bennington Battle Monument and 48 km from Bennington Museum, Wooded Wonder features a...
  • Parking

no reviews

from $339.02 Show details »

Rowemont in Jacksonville, USA

Rowemont

Holiday home in Jacksonville near Chesterfield, New Hampshire
Rowemont is situated in Jacksonville.
  • Parking
  • Tea/Coffee maker
  • Internet facilities
  • Shower
  • Bath

no reviews

from $159.00 Show details »

Austrian Haus Lodge in West Dover, USA

Austrian Haus Lodge

Lodge in West Dover near Chesterfield, New Hampshire , 6 Abroad Road
Located 4 miles from skiing on Mount Snow, this Vermont lodge features an indoor pool and a sauna.
  • Parking
  • Sauna
  • Indoor pool
  • Swimming pool
  • Swimming Pool

Pleasant 53 Reviews 7.0

from $127.50 Show details »

Valley View: Forest Edge 189 in Dover, USA

Valley View: Forest Edge 189

Holiday home in Dover near Chesterfield, New Hampshire
Valley View: Forest Edge 189 is situated in Dover, 44 km from Adams.
  • Parking
  • Pets allowed
  • Tea/Coffee maker
  • TV
  • Telephone

Pleasant 4 Reviews 6.2

from $165.33 Show details »

Wardsboro Family Escape in Wardsboro, USA

Wardsboro Family Escape

Holiday home in Wardsboro near Chesterfield, New Hampshire
Featuring a hot tub, Wardsboro Family Escape is situated in Wardsboro.
  • Parking
  • Pets allowed
  • Tea/Coffee maker
  • Internet facilities
  • Shower

Good 4 Reviews 7.7

from $360.36 Show details »

Spacious Dover Home with Sauna Less Than 5 Miles to Ski! in Dover, USA

Spacious Dover Home with Sauna Less Than...

Holiday home in Dover near Chesterfield, New Hampshire
Situated in Dover, 32 km from Stratton Mountain and 48 km from Bennington Battle Monument, Spacious Dover Home with Sauna Less Than 5 Miles to Ski! pr...
  • Parking
  • Sauna

Exceptional 2 Reviews 10.0

from $459.00 Show details »

Johns Farmhouse in Mount Snow on 120 Acres! in Whitingham, USA

Johns Farmhouse in Mount Snow on 120 Acr...

Holiday home in Whitingham near Chesterfield, New Hampshire
Johns Farmhouse in Mount Snow on 120 Acres! is situated in Whitingham, 43 km from Bennington Battle Monument, 46 km from Stratton Mountain, as well as...
  • Parking
  • Internet facilities
  • Refrigerator
  • Toilet
  • Microwave

Superb 4 Reviews 9.5

from $397.86 Show details »

Dover Delight in West Dover, USA

Dover Delight

Holiday home in West Dover near Chesterfield, New Hampshire , 8 Pheasant Lane
Located in West Dover, 32 km from Stratton Mountain and 48 km from Bennington Battle Monument, Dover Delight provides accommodation with amenities suc...
  • Parking
  • Tea/Coffee maker
  • Internet facilities
  • TV
  • Refrigerator

no reviews

from $204.00 Show details »

2-Acre Ski Chalet with Deck 8 Mi to Mt Snow! in Wardsboro, USA

2-Acre Ski Chalet with Deck 8 Mi to Mt S...

Holiday home in Wardsboro near Chesterfield, New Hampshire
2-Acre Ski Chalet with Deck 8 Mi to Mt Snow! is set in Wardsboro, 47 km from Mount Equinox, 20 km from Mount Snow Resort, and 32 km from Molly Stark S...
  • Parking

no reviews

from $377.00 Show details »

Engel Haus in Wardsboro, USA

Engel Haus

Holiday home in Wardsboro near Chesterfield, New Hampshire
Set in Wardsboro, 20 km from Stratton Mountain, Engel Haus offers accommodation with a garden, free WiFi and an ATM.
  • Parking

Pleasant 1 Reviews 6.0

from $186.33 Show details »

A-Frame Retreat in Wardsboro, USA

A-Frame Retreat

Holiday home in Wardsboro near Chesterfield, New Hampshire
Set in Wardsboro, 29 km from Stratton Mountain and 47 km from Mount Equinox, A-Frame Retreat provides accommodation with amenities such as free WiFi a...
  • Parking
  • Pets allowed

no reviews

from $227.94 Show details »

Number of Holiday homes in Chesterfield 110
Average price per night $295.24
Lowest price per night $108.00
Highest price per night $741.00

Most popular Holiday-homes in Chesterfield

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

Cheapest Holiday-homes in Chesterfield

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

Most booked Holiday-homes in Chesterfield

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

Holiday homes in Chesterfield (New Hampshire), comfortable and familiar

Staying in a holiday or vacation home in Chesterfield 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 Chesterfield 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 Chesterfield 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