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Chesterfield Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

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Distance from

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

Lake house getaway on pristine Spofford Lake, New Hampshire

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Picturesque Lakefront Retreat at Spofford Lake, vacation rental in Chesterfield
Picturesque Lakefront Retreat at Spofford Lake, vacation rental in Chesterfield
Picturesque Lakefront Retreat at Spofford Lake, vacation rental in Chesterfield

Picturesque Lakefront Retreat at Spofford Lake

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Penthouse, Steps to the Sandy Beach & clear water, vacation rental in Chesterfield
Penthouse, Steps to the Sandy Beach & clear water, vacation rental in Chesterfield
Penthouse, Steps to the Sandy Beach & clear water, vacation rental in Chesterfield

Penthouse, Steps to the Sandy Beach & clear water

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Main House, Relax and enjoy the scenery, go and swim, fish or start your boat, vacation rental in Chesterfield
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat, vacation rental in Chesterfield
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat, vacation rental in Chesterfield

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, vacation rental in Chesterfield
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, vacation rental in Chesterfield
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, vacation rental in Chesterfield

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

Rental Home
4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, vacation rental in Chesterfield
Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, vacation rental in Chesterfield
Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, vacation rental in Chesterfield

Victorian Lakefront Cottage With Spectacular Sunrise View Of Water

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Peaceful lake front home on beautiful Spofford Lake!, vacation rental in Chesterfield
Peaceful lake front home on beautiful Spofford Lake!, vacation rental in Chesterfield
Peaceful lake front home on beautiful Spofford Lake!, vacation rental in Chesterfield

Peaceful lake front home on beautiful Spofford Lake!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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The following properties within 20 miles of Chesterfield match all your filters:
Serenity Cottage in Southern Vermont…, vacation rental in Chesterfield
Serenity Cottage in Southern Vermont…, vacation rental in Chesterfield
Serenity Cottage in Southern Vermont…, vacation rental in Chesterfield

Serenity Cottage in Southern Vermont…

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Mountain Top Escape, vacation rental in Chesterfield
Mountain Top Escape, vacation rental in Chesterfield
Mountain Top Escape, vacation rental in Chesterfield

Mountain Top Escape

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Romantic Rock River Cottage with Hot Tub, Fireplace & Beach - Newfane VT, vacation rental in Chesterfield
Romantic Rock River Cottage with Hot Tub, Fireplace & Beach - Newfane VT, vacation rental in Chesterfield
Romantic Rock River Cottage with Hot Tub, Fireplace & Beach - Newfane VT, vacation rental in Chesterfield

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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Family Friendly Hilltop House In Putney Vermont, vacation rental in Chesterfield
Family Friendly Hilltop House In Putney Vermont, vacation rental in Chesterfield
Family Friendly Hilltop House In Putney Vermont, vacation rental in Chesterfield

Family Friendly Hilltop House In Putney Vermont

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful lake side get away, quiet, and peaceful., vacation rental in Chesterfield
Beautiful lake side get away, quiet, and peaceful., vacation rental in Chesterfield
Beautiful lake side get away, quiet, and peaceful., vacation rental in Chesterfield

Beautiful lake side get away, quiet, and peaceful.

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cabin Retreat in Southern Vermont, vacation rental in Chesterfield
Cabin Retreat in Southern Vermont, vacation rental in Chesterfield
Cabin Retreat in Southern Vermont, vacation rental in Chesterfield

Cabin Retreat in Southern Vermont

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Fully Furnished 2bdrm/Pet Friendly!, vacation rental in Chesterfield
Fully Furnished 2bdrm/Pet Friendly!, vacation rental in Chesterfield
Fully Furnished 2bdrm/Pet Friendly!, vacation rental in Chesterfield

Fully Furnished 2bdrm/Pet Friendly!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Fully furnished/everything included/Pet Friendly!, vacation rental in Chesterfield
Fully furnished/everything included/Pet Friendly!, vacation rental in Chesterfield
Fully furnished/everything included/Pet Friendly!, vacation rental in Chesterfield

Fully furnished/everything included/Pet Friendly!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Downtown apartment ideal location to everything, vacation rental in Chesterfield
Downtown apartment ideal location to everything, vacation rental in Chesterfield
Downtown apartment ideal location to everything, vacation rental in Chesterfield

Downtown apartment ideal location to everything

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Artsy, Pet-Friendly Studio with a  Forest in the backyard, vacation rental in Chesterfield
Artsy, Pet-Friendly Studio with a  Forest in the backyard, vacation rental in Chesterfield
Artsy, Pet-Friendly Studio with a  Forest in the backyard, vacation rental in Chesterfield

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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You have found a clean and bright home on the water., vacation rental in Chesterfield
You have found a clean and bright home on the water., vacation rental in Chesterfield
You have found a clean and bright home on the water., vacation rental in Chesterfield

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Tranquil NH Cabin on Connecticut River, vacation rental in Chesterfield
Tranquil NH Cabin on Connecticut River, vacation rental in Chesterfield
Tranquil NH Cabin on Connecticut River, vacation rental in Chesterfield

Tranquil NH Cabin on Connecticut River

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!, vacation rental in Chesterfield
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!, vacation rental in Chesterfield
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!, vacation rental in Chesterfield

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Wonderful Private Home In West Brattleboro Off Of Route 9, vacation rental in Chesterfield
Wonderful Private Home In West Brattleboro Off Of Route 9, vacation rental in Chesterfield
Wonderful Private Home In West Brattleboro Off Of Route 9, vacation rental in Chesterfield

Wonderful Private Home In West Brattleboro Off Of Route 9

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Story Book Lake Front Chateau with Private Beach!, vacation rental in Chesterfield
Story Book Lake Front Chateau with Private Beach!, vacation rental in Chesterfield
Story Book Lake Front Chateau with Private Beach!, vacation rental in Chesterfield

Story Book Lake Front Chateau with Private Beach!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Hike & Swim On-Site: Cozy Falls Brook Cabin, vacation rental in Chesterfield
Hike & Swim On-Site: Cozy Falls Brook Cabin, vacation rental in Chesterfield
Hike & Swim On-Site: Cozy Falls Brook Cabin, vacation rental in Chesterfield

Hike & Swim On-Site: Cozy Falls Brook Cabin

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!, vacation rental in Chesterfield
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!, vacation rental in Chesterfield
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!, vacation rental in Chesterfield

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

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Year Round Mountain Retreat, vacation rental in Chesterfield
Year Round Mountain Retreat, vacation rental in Chesterfield
Year Round Mountain Retreat, vacation rental in Chesterfield

Year Round Mountain Retreat

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Renovated Church Sanctuary: Ski and Swim, Relax, Cook, Gather., vacation rental in Chesterfield
Renovated Church Sanctuary: Ski and Swim, Relax, Cook, Gather., vacation rental in Chesterfield
Renovated Church Sanctuary: Ski and Swim, Relax, Cook, Gather., vacation rental in Chesterfield

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hilltop Home with Great Views, vacation rental in Chesterfield
Hilltop Home with Great Views, vacation rental in Chesterfield
Hilltop Home with Great Views, vacation rental in Chesterfield

Hilltop Home with Great Views

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Peaceful, Beautiful, Comfortable Modern Cape With Spectacular Mountain Views, vacation rental in Chesterfield
Peaceful, Beautiful, Comfortable Modern Cape With Spectacular Mountain Views, vacation rental in Chesterfield
Peaceful, Beautiful, Comfortable Modern Cape With Spectacular Mountain Views, vacation rental in Chesterfield

Peaceful, Beautiful, Comfortable Modern Cape With Spectacular Mountain Views

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake, vacation rental in Chesterfield
Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake, vacation rental in Chesterfield
Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake, vacation rental in Chesterfield

Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Bright, Large, Spacious Family Home, vacation rental in Chesterfield
Bright, Large, Spacious Family Home, vacation rental in Chesterfield
Bright, Large, Spacious Family Home, vacation rental in Chesterfield

Bright, Large, Spacious Family Home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Modern House, Beautiful Deck/Patio Overlooking Golf Course & Mountains, vacation rental in Chesterfield
Spacious Modern House, Beautiful Deck/Patio Overlooking Golf Course & Mountains, vacation rental in Chesterfield
Spacious Modern House, Beautiful Deck/Patio Overlooking Golf Course & Mountains, vacation rental in Chesterfield

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful 5-Bedroom Upscale Country Home With Home Theater, vacation rental in Chesterfield
Beautiful 5-Bedroom Upscale Country Home With Home Theater, vacation rental in Chesterfield
Beautiful 5-Bedroom Upscale Country Home With Home Theater, vacation rental in Chesterfield

Beautiful 5-Bedroom Upscale Country Home With Home Theater

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Lake Front Scenic Home  6 bdrm with  3 &1/2 bath, vacation rental in Chesterfield
Lake Front Scenic Home  6 bdrm with  3 &1/2 bath, vacation rental in Chesterfield
Lake Front Scenic Home  6 bdrm with  3 &1/2 bath, vacation rental in Chesterfield

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

Rental Home
7 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Lake Front Bldg. Friendly Secluded/Wooded w. 6 Bedrms, vacation rental in Chesterfield
Lake Front Bldg. Friendly Secluded/Wooded w. 6 Bedrms, vacation rental in Chesterfield
Lake Front Bldg. Friendly Secluded/Wooded w. 6 Bedrms, vacation rental in Chesterfield

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

Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Fully furnished/Pet Friendly!, vacation rental in Chesterfield
Fully furnished/Pet Friendly!, vacation rental in Chesterfield
Fully furnished/Pet Friendly!, vacation rental in Chesterfield

Fully furnished/Pet Friendly!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy home in Brattleboro, vacation rental in Chesterfield
Cozy home in Brattleboro, vacation rental in Chesterfield
Cozy home in Brattleboro, vacation rental in Chesterfield

Cozy home in Brattleboro

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Home Near Downtown, Shops, and Restaurants., vacation rental in Chesterfield
Cozy Home Near Downtown, Shops, and Restaurants., vacation rental in Chesterfield
Cozy Home Near Downtown, Shops, and Restaurants., vacation rental in Chesterfield

Cozy Home Near Downtown, Shops, and Restaurants.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private, cozy, and charming cabin just minutes from town., vacation rental in Chesterfield
Private, cozy, and charming cabin just minutes from town., vacation rental in Chesterfield
Private, cozy, and charming cabin just minutes from town., vacation rental in Chesterfield

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options, vacation rental in Chesterfield
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options, vacation rental in Chesterfield
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options, vacation rental in Chesterfield

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

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Charming Putney Home: Porch, Grill & Hiking Trails, vacation rental in Chesterfield
Charming Putney Home: Porch, Grill & Hiking Trails, vacation rental in Chesterfield
Charming Putney Home: Porch, Grill & Hiking Trails, vacation rental in Chesterfield

Charming Putney Home: Porch, Grill & Hiking Trails

Rental Home
5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Spacious Estate w/ Courtyard: 2 Miles to Downtown!, vacation rental in Chesterfield
Spacious Estate w/ Courtyard: 2 Miles to Downtown!, vacation rental in Chesterfield
Spacious Estate w/ Courtyard: 2 Miles to Downtown!, vacation rental in Chesterfield

Spacious Estate w/ Courtyard: 2 Miles to Downtown!

Rental Home
9 bedrooms
9 bathrooms
Sleeps 15
Match: Sleeps
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Magical Lakefront Home in Forest Lake, vacation rental in Chesterfield
Magical Lakefront Home in Forest Lake, vacation rental in Chesterfield
Magical Lakefront Home in Forest Lake, vacation rental in Chesterfield

Magical Lakefront Home in Forest Lake

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Cozy 1-bedroom apartment in delightful Brattleboro, vacation rental in Chesterfield
Cozy 1-bedroom apartment in delightful Brattleboro, vacation rental in Chesterfield
Cozy 1-bedroom apartment in delightful Brattleboro, vacation rental in Chesterfield

Cozy 1-bedroom apartment in delightful Brattleboro

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Sauna and Mountain Views, the Perfect Cozy Vermont Getaway, vacation rental in Chesterfield
Sauna and Mountain Views, the Perfect Cozy Vermont Getaway, vacation rental in Chesterfield
Sauna and Mountain Views, the Perfect Cozy Vermont Getaway, vacation rental in Chesterfield

Sauna and Mountain Views, the Perfect Cozy Vermont Getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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HeART Barn, 35-60 m. to skiing * Mt. Snow, Stratton, Okemo, Magic & Bromley, vacation rental in Chesterfield
HeART Barn, 35-60 m. to skiing * Mt. Snow, Stratton, Okemo, Magic & Bromley, vacation rental in Chesterfield
HeART Barn, 35-60 m. to skiing * Mt. Snow, Stratton, Okemo, Magic & Bromley, vacation 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
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Fully furnished 2 bdr apartment, vacation rental in Chesterfield
Fully furnished 2 bdr apartment, vacation rental in Chesterfield
Fully furnished 2 bdr apartment, vacation rental in Chesterfield

Fully furnished 2 bdr apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Showing results 1-46 of 46
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