We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chesterfield Holiday Apartments

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
46 rentals in Chesterfield.
Lake house getaway on pristine Spofford Lake, New Hampshire, holiday rental in Chesterfield
Lake house getaway on pristine Spofford Lake, New Hampshire, holiday rental in Chesterfield
Lake house getaway on pristine Spofford Lake, New Hampshire, holiday rental in Chesterfield

Lake house getaway on pristine Spofford Lake, New Hampshire

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Picturesque Lakefront Retreat at Spofford Lake, holiday rental in Chesterfield
Picturesque Lakefront Retreat at Spofford Lake, holiday rental in Chesterfield
Picturesque Lakefront Retreat at Spofford Lake, holiday rental in Chesterfield

Picturesque Lakefront Retreat at Spofford Lake

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Penthouse, Steps to the Sandy Beach & clear water, holiday rental in Chesterfield
Penthouse, Steps to the Sandy Beach & clear water, holiday rental in Chesterfield
Penthouse, Steps to the Sandy Beach & clear water, holiday rental in Chesterfield

Penthouse, Steps to the Sandy Beach & clear water

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat, holiday rental in Chesterfield
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat, holiday rental in Chesterfield
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat, holiday rental in Chesterfield

Main House, Relax and enjoy the scenery, go and swim, fish or start your boat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, holiday rental in Chesterfield
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, holiday rental in Chesterfield
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, holiday rental in Chesterfield

Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, holiday rental in Chesterfield
Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, holiday rental in Chesterfield
Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, holiday rental in Chesterfield

Victorian Lakefront Cottage With Spectacular Sunrise View Of Water

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Peaceful lake front home on beautiful Spofford Lake!, holiday rental in Chesterfield
Peaceful lake front home on beautiful Spofford Lake!, holiday rental in Chesterfield
Peaceful lake front home on beautiful Spofford Lake!, holiday rental in Chesterfield

Peaceful lake front home on beautiful Spofford Lake!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
The following properties within 32 kms of Chesterfield match all your filters:
Serenity Cottage in Southern Vermont…, holiday rental in Chesterfield
Serenity Cottage in Southern Vermont…, holiday rental in Chesterfield
Serenity Cottage in Southern Vermont…, holiday rental in Chesterfield

Serenity Cottage in Southern Vermont…

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Mountain Top Escape, holiday rental in Chesterfield
Mountain Top Escape, holiday rental in Chesterfield
Mountain Top Escape, holiday rental in Chesterfield

Mountain Top Escape

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Romantic Rock River Cottage with Hot Tub, Fireplace & Beach - Newfane VT, holiday rental in Chesterfield
Romantic Rock River Cottage with Hot Tub, Fireplace & Beach - Newfane VT, holiday rental in Chesterfield
Romantic Rock River Cottage with Hot Tub, Fireplace & Beach - Newfane VT, holiday rental in Chesterfield

Romantic Rock River Cottage with Hot Tub, Fireplace & Beach - Newfane VT

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Family Friendly Hilltop House In Putney Vermont, holiday rental in Chesterfield
Family Friendly Hilltop House In Putney Vermont, holiday rental in Chesterfield
Family Friendly Hilltop House In Putney Vermont, holiday rental in Chesterfield

Family Friendly Hilltop House In Putney Vermont

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Beautiful lake side get away, quiet, and peaceful., holiday rental in Chesterfield
Beautiful lake side get away, quiet, and peaceful., holiday rental in Chesterfield
Beautiful lake side get away, quiet, and peaceful., holiday rental in Chesterfield

Beautiful lake side get away, quiet, and peaceful.

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Cabin Retreat in Southern Vermont, holiday rental in Chesterfield
Cabin Retreat in Southern Vermont, holiday rental in Chesterfield
Cabin Retreat in Southern Vermont, holiday rental in Chesterfield

Cabin Retreat in Southern Vermont

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Fully Furnished 2bdrm/Pet Friendly!, holiday rental in Chesterfield
Fully Furnished 2bdrm/Pet Friendly!, holiday rental in Chesterfield
Fully Furnished 2bdrm/Pet Friendly!, holiday rental in Chesterfield

Fully Furnished 2bdrm/Pet Friendly!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Fully furnished/everything included/Pet Friendly!, holiday rental in Chesterfield
Fully furnished/everything included/Pet Friendly!, holiday rental in Chesterfield
Fully furnished/everything included/Pet Friendly!, holiday rental in Chesterfield

Fully furnished/everything included/Pet Friendly!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Downtown apartment ideal location to everything, holiday rental in Chesterfield
Downtown apartment ideal location to everything, holiday rental in Chesterfield
Downtown apartment ideal location to everything, holiday rental in Chesterfield

Downtown apartment ideal location to everything

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Artsy, Pet-Friendly Studio with a  Forest in the backyard, holiday rental in Chesterfield
Artsy, Pet-Friendly Studio with a  Forest in the backyard, holiday rental in Chesterfield
Artsy, Pet-Friendly Studio with a  Forest in the backyard, holiday rental in Chesterfield

Artsy, Pet-Friendly Studio with a Forest in the backyard

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
You have found a clean and bright home on the water., holiday rental in Chesterfield
You have found a clean and bright home on the water., holiday rental in Chesterfield
You have found a clean and bright home on the water., holiday rental in Chesterfield

You have found a clean and bright home on the water.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Tranquil NH Cabin on Connecticut River, holiday rental in Chesterfield
Tranquil NH Cabin on Connecticut River, holiday rental in Chesterfield
Tranquil NH Cabin on Connecticut River, holiday rental in Chesterfield

Tranquil NH Cabin on Connecticut River

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!, holiday rental in Chesterfield
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!, holiday rental in Chesterfield
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!, holiday rental in Chesterfield

Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Wonderful Private Home In West Brattleboro Off Of Route 9, holiday rental in Chesterfield
Wonderful Private Home In West Brattleboro Off Of Route 9, holiday rental in Chesterfield
Wonderful Private Home In West Brattleboro Off Of Route 9, holiday rental in Chesterfield

Wonderful Private Home In West Brattleboro Off Of Route 9

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Story Book Lake Front Chateau with Private Beach!, holiday rental in Chesterfield
Story Book Lake Front Chateau with Private Beach!, holiday rental in Chesterfield
Story Book Lake Front Chateau with Private Beach!, holiday rental in Chesterfield

Story Book Lake Front Chateau with Private Beach!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Hike & Swim On-Site: Cozy Falls Brook Cabin, holiday rental in Chesterfield
Hike & Swim On-Site: Cozy Falls Brook Cabin, holiday rental in Chesterfield
Hike & Swim On-Site: Cozy Falls Brook Cabin, holiday rental in Chesterfield

Hike & Swim On-Site: Cozy Falls Brook Cabin

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!, holiday rental in Chesterfield
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!, holiday rental in Chesterfield
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!, holiday rental in Chesterfield

Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Year Round Mountain Retreat, holiday rental in Chesterfield
Year Round Mountain Retreat, holiday rental in Chesterfield
Year Round Mountain Retreat, holiday rental in Chesterfield

Year Round Mountain Retreat

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Renovated Church Sanctuary: Ski and Swim, Relax, Cook, Gather., holiday rental in Chesterfield
Renovated Church Sanctuary: Ski and Swim, Relax, Cook, Gather., holiday rental in Chesterfield
Renovated Church Sanctuary: Ski and Swim, Relax, Cook, Gather., holiday rental in Chesterfield

Renovated Church Sanctuary: Ski and Swim, Relax, Cook, Gather.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Hilltop Home with Great Views, holiday rental in Chesterfield
Hilltop Home with Great Views, holiday rental in Chesterfield
Hilltop Home with Great Views, holiday rental in Chesterfield

Hilltop Home with Great Views

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Peaceful, Beautiful, Comfortable Modern Cape With Spectacular Mountain Views, holiday rental in Chesterfield
Peaceful, Beautiful, Comfortable Modern Cape With Spectacular Mountain Views, holiday rental in Chesterfield
Peaceful, Beautiful, Comfortable Modern Cape With Spectacular Mountain Views, holiday rental in Chesterfield

Peaceful, Beautiful, Comfortable Modern Cape With Spectacular Mountain Views

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake, holiday rental in Chesterfield
Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake, holiday rental in Chesterfield
Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake, holiday rental in Chesterfield

Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Bright, Large, Spacious Family Home, holiday rental in Chesterfield
Bright, Large, Spacious Family Home, holiday rental in Chesterfield
Bright, Large, Spacious Family Home, holiday rental in Chesterfield

Bright, Large, Spacious Family Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Spacious Modern House, Beautiful Deck/Patio Overlooking Golf Course & Mountains, holiday rental in Chesterfield
Spacious Modern House, Beautiful Deck/Patio Overlooking Golf Course & Mountains, holiday rental in Chesterfield
Spacious Modern House, Beautiful Deck/Patio Overlooking Golf Course & Mountains, holiday rental in Chesterfield

Spacious Modern House, Beautiful Deck/Patio Overlooking Golf Course & Mountains

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Beautiful 5-Bedroom Upscale Country Home With Home Theater, holiday rental in Chesterfield
Beautiful 5-Bedroom Upscale Country Home With Home Theater, holiday rental in Chesterfield
Beautiful 5-Bedroom Upscale Country Home With Home Theater, holiday rental in Chesterfield

Beautiful 5-Bedroom Upscale Country Home With Home Theater

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Lake Front Scenic Home  6 bdrm with  3 &1/2 bath, holiday rental in Chesterfield
Lake Front Scenic Home  6 bdrm with  3 &1/2 bath, holiday rental in Chesterfield
Lake Front Scenic Home  6 bdrm with  3 &1/2 bath, holiday rental in Chesterfield

Lake Front Scenic Home 6 bdrm with 3 &1/2 bath

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Lake Front Bldg. Friendly Secluded/Wooded w. 6 Bedrms, holiday rental in Chesterfield
Lake Front Bldg. Friendly Secluded/Wooded w. 6 Bedrms, holiday rental in Chesterfield
Lake Front Bldg. Friendly Secluded/Wooded w. 6 Bedrms, holiday rental in Chesterfield

Lake Front Bldg. Friendly Secluded/Wooded w. 6 Bedrms

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Fully furnished 2 bdr apartment, holiday rental in Chesterfield
Fully furnished 2 bdr apartment, holiday rental in Chesterfield
Fully furnished 2 bdr apartment, holiday rental in Chesterfield

Fully furnished 2 bdr apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
HeART Barn, 35-60 m. to skiing * Mt. Snow, Stratton, Okemo, Magic & Bromley, holiday rental in Chesterfield
HeART Barn, 35-60 m. to skiing * Mt. Snow, Stratton, Okemo, Magic & Bromley, holiday rental in Chesterfield
HeART Barn, 35-60 m. to skiing * Mt. Snow, Stratton, Okemo, Magic & Bromley, holiday rental in Chesterfield

HeART Barn, 35-60 m. to skiing * Mt. Snow, Stratton, Okemo, Magic & Bromley

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Sauna and Mountain Views, the Perfect Cozy Vermont Getaway, holiday rental in Chesterfield
Sauna and Mountain Views, the Perfect Cozy Vermont Getaway, holiday rental in Chesterfield
Sauna and Mountain Views, the Perfect Cozy Vermont Getaway, holiday rental in Chesterfield

Sauna and Mountain Views, the Perfect Cozy Vermont Getaway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Cozy 1-bedroom apartment in delightful Brattleboro, holiday rental in Chesterfield
Cozy 1-bedroom apartment in delightful Brattleboro, holiday rental in Chesterfield
Cozy 1-bedroom apartment in delightful Brattleboro, holiday rental in Chesterfield

Cozy 1-bedroom apartment in delightful Brattleboro

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Magical Lakefront Home in Forest Lake, holiday rental in Chesterfield
Magical Lakefront Home in Forest Lake, holiday rental in Chesterfield
Magical Lakefront Home in Forest Lake, holiday rental in Chesterfield

Magical Lakefront Home in Forest Lake

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Spacious Estate w/ Courtyard: 2 Miles to Downtown!, holiday rental in Chesterfield
Spacious Estate w/ Courtyard: 2 Miles to Downtown!, holiday rental in Chesterfield
Spacious Estate w/ Courtyard: 2 Miles to Downtown!, holiday rental in Chesterfield

Spacious Estate w/ Courtyard: 2 Miles to Downtown!

Holiday Rental House
9 bedrooms
9 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Charming Putney Home: Porch, Grill & Hiking Trails, holiday rental in Chesterfield
Charming Putney Home: Porch, Grill & Hiking Trails, holiday rental in Chesterfield
Charming Putney Home: Porch, Grill & Hiking Trails, holiday rental in Chesterfield

Charming Putney Home: Porch, Grill & Hiking Trails

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options, holiday rental in Chesterfield
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options, holiday rental in Chesterfield
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options, holiday rental in Chesterfield

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Private, cozy, and charming cabin just minutes from town., holiday rental in Chesterfield
Private, cozy, and charming cabin just minutes from town., holiday rental in Chesterfield
Private, cozy, and charming cabin just minutes from town., holiday rental in Chesterfield

Private, cozy, and charming cabin just minutes from town.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Cozy Home Near Downtown, Shops, and Restaurants., holiday rental in Chesterfield
Cozy Home Near Downtown, Shops, and Restaurants., holiday rental in Chesterfield
Cozy Home Near Downtown, Shops, and Restaurants., holiday rental in Chesterfield

Cozy Home Near Downtown, Shops, and Restaurants.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Cozy home in Brattleboro, holiday rental in Chesterfield
Cozy home in Brattleboro, holiday rental in Chesterfield
Cozy home in Brattleboro, holiday rental in Chesterfield

Cozy home in Brattleboro

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Fully furnished/Pet Friendly!, holiday rental in Chesterfield
Fully furnished/Pet Friendly!, holiday rental in Chesterfield
Fully furnished/Pet Friendly!, holiday rental in Chesterfield

Fully furnished/Pet Friendly!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stayz.com.au logo
Showing results 1-46 of 46
Frequently Asked Questions about Chesterfield