Airbnb, Vacation Rentals in Chesterfield, MA

Compare 1,034 available lakefront holiday vacation home properties, starts from $28

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Airbnb, Vacation rentals and hotel deals in Chesterfield, MA

The Dewey
The Dewey
The Dewey
The Dewey
9.1 (63 reviews)
The Dewey
B & B · 2 Guests · 1 Bedroom
$145 /night
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Quality Inn Westfield - Springfield
Quality Inn Westfield - Springfield
Quality Inn Westfield - Springfield
Quality Inn Westfield - Springfield
6.9 (124 reviews)
Quality Inn Westfield - Springfield
Hotel · 2 Guests · 1 Bedroom
$103 /night
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Courtyard by Marriott West Springfield
Courtyard by Marriott West Springfield
Courtyard by Marriott West Springfield
Courtyard by Marriott West Springfield
8.8 (149 reviews)
Courtyard by Marriott West Springfield
Hotel · 2 Guests · 1 Bedroom
$152 /night
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Hampton Inn Westfield
Hampton Inn Westfield
Hampton Inn Westfield
Hampton Inn Westfield
7.4 (70 reviews)
Hampton Inn Westfield
Hotel · 2 Guests · 1 Bedroom
$145 /night
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Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
8.4 (224 reviews)
Best Western Plus Berkshire Hills Inn & Suites
Hotel · 2 Guests · 1 Bedroom
$132 /night
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Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
7.7 (316 reviews)
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$142 /night
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Berkshire Inn
Berkshire Inn
Berkshire Inn
Berkshire Inn
7.8 (217 reviews)
Berkshire Inn
Motel · 2 Guests · 1 Bedroom
$75 /night
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Quality Inn West Springfield
Quality Inn West Springfield
Quality Inn West Springfield
Quality Inn West Springfield
7.5 (352 reviews)
Quality Inn West Springfield
Hotel · 2 Guests · 1 Bedroom
$87 /night
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Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
6.2 (474 reviews)
Econo Lodge Lee - Great Barrington
Motel · 2 Guests · 1 Bedroom
$63 /night
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Elm Motel
Elm Motel
Elm Motel
Elm Motel
6.7 (24 reviews)
Elm Motel
Motel · 2 Guests · 1 Bedroom
$89 /night
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Elm Suite - Private Bathroom with Jacuzzi in front of Smith College
Elm Suite - Private Bathroom with Jacuzzi in front of Smith College
Elm Suite - Private Bathroom with Jacuzzi in front of Smith College
Elm Suite - Private Bathroom with Jacuzzi in front of Smith College
10 (4 reviews)
Elm Suite - Private Bathroom with Jacuzzi in front of Smith College
Apartment · 2 Guests · 1 Bedroom
$125 /night*
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Star gazer no city lights
Star gazer no city lights
Star gazer no city lights
Star gazer no city lights
9.6 (8 reviews)
Star gazer no city lights
Apartment · 2 Guests · 1 Bedroom
$145 /night*
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D. Hotel Suites & Spa
D. Hotel Suites & Spa
D. Hotel Suites & Spa
D. Hotel Suites & Spa
9.0 (1006 reviews)
D. Hotel Suites & Spa
Hotel · 2 Guests · 1 Bedroom
$126 /night
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Pilgrim Inn
Pilgrim Inn
Pilgrim Inn
Pilgrim Inn
6.2 (59 reviews)
Pilgrim Inn
Inn · 2 Guests · 1 Bedroom
$76 /night
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Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
9.1 (350 reviews)
Hampton Inn & Suites Berkshires-Lenox
Hotel · 2 Guests · 1 Bedroom
$155 /night
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Riverdale Inn
Riverdale Inn
Riverdale Inn
Riverdale Inn
5.9 (293 reviews)
Riverdale Inn
Hotel · 2 Guests · 1 Bedroom
$102 /night
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Blooming Inn
Blooming Inn
Blooming Inn
Blooming Inn
8.6 (29 reviews)
Blooming Inn
Guest house · 2 Guests · 1 Bedroom
$81 /night
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Riverdale Inn
Riverdale Inn
Riverdale Inn
Riverdale Inn
7.3 (4 reviews)
Riverdale Inn
Hotel · 2 Guests · 1 Bedroom
$102 /night
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Best Western Springfield West Inn
Best Western Springfield West Inn
Best Western Springfield West Inn
Best Western Springfield West Inn
7.8 (423 reviews)
Best Western Springfield West Inn
Hotel · 2 Guests · 1 Bedroom
$105 /night
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Comfort Inn & Suites
Comfort Inn & Suites
Comfort Inn & Suites
Comfort Inn & Suites
8.9 (307 reviews)
Comfort Inn & Suites
Hotel · 2 Guests · 1 Bedroom
$138 /night
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Vacation Destinations Near Chesterfield, MA

Airbnb, Holiday Lakefront House with Air Conditioning in Chesterfield, MA

Naomi's Inn Bed & Breakfast
Naomi's Inn Bed & Breakfast
Naomi's Inn Bed & Breakfast
Naomi's Inn Bed & Breakfast
Air Conditioning
9.0 (75 reviews)
Naomi's Inn Bed & Breakfast
B & B · 2 Guests · 1 Bedroom
$395 /night
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The Trail in Adams - Berkshires' Art Hotel
The Trail in Adams - Berkshires' Art Hotel
The Trail in Adams - Berkshires' Art Hotel
The Trail in Adams - Berkshires' Art Hotel
Air Conditioning
9.5 (12 reviews)
The Trail in Adams - Berkshires' Art Hotel
B & B · 2 Guests · 1 Bedroom
$245 /night
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The Dewey
The Dewey
The Dewey
The Dewey
Air Conditioning
9.1 (63 reviews)
The Dewey
B & B · 2 Guests · 1 Bedroom
$145 /night
View deal
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What Are The Most Popular Amenities in Chesterfield, MA?
Amenity Overview in Chesterfield, MA
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The above reveals the top rental amenities and the property numbers associated with each of them in Chesterfield. In Chesterfield, 488 rentals offer Internet or Wifi, 471 rentals offer No Smoking, 464 rentals offer Bed linens provided. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Hot Tub, Pool.
How Does The Vacation Home Rental Price Look Like in Chesterfield, MA?
Vacation House & Condo Rental Price Information in Chesterfield, MA
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The graph shows the percentages of vacation homes in each price bucket. Chesterfield has the largest percentage (14.98%) of homes in $150 - $200 price range.
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$500 +
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Which Accommodations Should I Pick in Chesterfield, MA?
Most Picked Accommodations in Chesterfield, MA
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In Chesterfield, 55.13% of listings are House, which is the most popular accommodation out of 21 total accommodation types. Avg price per night for House is around $354. And the most searched amenities for House accommodation is Hot Tub.The least popular accommodation in Chesterfield is Mill rentals
How Many Rental Accommodations Are Pets Friendly in Chesterfield, MA?
Pets Allowed vs Not Allowed in Chesterfield, MA
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31.14% of vacation homes in Chesterfield are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Trail Recommendations in Chesterfield, MA Area?
Best Trails In Chesterfield, MA
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The most visited trails here in Chesterfield are: Keystone Arch Bridges Trail, Glendale Falls Trail, Orange Trail, Pink Trail, Falls Trail, Sanderson Brook Falls Trail, Upper Highland Lake Trail, D.A.R. State Forest, William Cullen Bryant Homestead Trail, Chesterfield Gorge.
Best Campgrounds in Chesterfield, MA?
Campgrounds Recommendations In Chesterfield, MA
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For campgrounds in Chesterfield, here are our recommendations: Woodland Hills Campground, Pine Hollow Campground, Clarksburg Campground, Prospect Lake Park Campground, Tolland State Forest Campground, Northampton / Springfield KOA, Erving State Forest Campground, Mohawk Trail State Forest Campground, Hinsdale Campground at Thicket Hill Village, Indian Hollow Campground.
Which Airports Should I Choose To Get To Chesterfield, MA?
Suggested Airports in Chesterfield, MA
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1 airport(s) close to Chesterfield are:

Airbnb, Holiday Lakefront House with Full Kitchen, and Other Rental Options in Chesterfield, MA

Beautiful, peaceful modern home in a wooded area with lake access
Beautiful, peaceful modern home in a wooded area with lake access
Beautiful, peaceful modern home in a wooded area with lake access
Beautiful, peaceful modern home in a wooded area with lake access
Full Kitchen
10 (14 reviews)
Beautiful, peaceful modern home in a wooded area with lake access
Holiday home · 2 Guests · 1 Bedroom
$425 /night*
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Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
Full Kitchen
9.8 (82 reviews)
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
Holiday home · 2 Guests · 1 Bedroom
$292 /night*
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In the Heart of Everything
In the Heart of Everything
In the Heart of Everything
In the Heart of Everything
Full Kitchen
9.8 (13 reviews)
In the Heart of Everything
Holiday home · 2 Guests · 1 Bedroom
$168 /night*
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Airbnb, Vacation Condo with Pool, and Other Rental Options in Chesterfield, MA

Quiet Neighborhood, For Bird Lovers
Quiet Neighborhood, For Bird Lovers
Quiet Neighborhood, For Bird Lovers
Quiet Neighborhood, For Bird Lovers
Pool
10 (40 reviews)
Quiet Neighborhood, For Bird Lovers
Apartment · 2 Guests · 1 Bedroom
$150 /night*
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Sun filled pool house with vaulted ceilings beautiful in ground pool and gardens
Sun filled pool house with vaulted ceilings beautiful in ground pool and gardens
Sun filled pool house with vaulted ceilings beautiful in ground pool and gardens
Sun filled pool house with vaulted ceilings beautiful in ground pool and gardens
Pool
10 (32 reviews)
Sun filled pool house with vaulted ceilings beautiful in ground pool and gardens
Apartment · 2 Guests · 1 Bedroom
$249 /night*
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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