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Chesterfield Vacation Travel Guide

Accommodation in Chesterfield

As there are no Chesterfield lodgings listed with Expedia, you may find it convenient to stay in West Chesterfield, just 1 mile (2 kilometers) away. The Chesterfield Inn and Riverside Hotel, an Ascend Hotel Collection Member are the most popular places to stay in West Chesterfield.

It’s easy to book the getaway of your dreams when you search through our selection of Chesterfield vacations. Our goal? To create the perfect trip for you by providing the largest selection of vacation packages. Confidently book your getaway thanks to our trustworthy recommendations and verified consumer reviews from travelers just like you. Personalize your Chesterfield package with our myriad of hotel rooms and flight tickets, which help to create a vacation specifically for you. Simply sort through our selection and pick and choose the elements that best suit your preferences and price range.

Because we offer the best rates, you can book your travel reservations knowing you won’t find lower prices elsewhere. These discounts are so great, you’ll feel like you gained the title of the ultimate bargain hunter with our Chesterfield vacation package deals. Whether you’re looking to book multiple flights, stay at the fanciest hotel, or explore the hottest local attractions, you’ll find discounted travel arrangements within your budget right here. You shouldn’t have a care in the world when you go on vacation, so our discounts allow you to rest easy without giving your bank account a second thought. Save money on your vacation today and revel in your much-deserved getaway tomorrow.


Top Hotel Deals

See all 93 Hotels in Chesterfield
$119
Riverside Hotel, an Ascend Hotel Collection Member

Riverside Hotel, an Ascend Hotel Collection Member

20 Riverside Drive, West Chesterfield
4.7
of 5, from 27 reviews
2.5 out of 5.0

Located in the heart of West Chesterfield, this hotel is 0.2 mi (0.3 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Madame Sherris Castle Ruins and Madame Sherri Forest. Brattleboro Common and Actors Theatre Playhouse are also within 3 mi (5 km).

$59
Quality Inn & Conference Center

Quality Inn & Conference Center

1380 Putney Road, Brattleboro
2.8
of 5, from 142 reviews
2.5 out of 5.0

Situated in Brattleboro, this hotel is 0.8 mi (1.3 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro Museum & Art Center. Madame Sherris Castle Ruins and Madame Sherri Forest are also within 6 mi (10 km).

$70
Colonial Motel And Spa

Colonial Motel And Spa

889 Putney Rd, Brattleboro
3.3
of 5, from 232 reviews
3.0 out of 5.0

Located in the heart of Brattleboro, this motel is 0.7 mi (1.1 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro Museum & Art Center. Estey Organ Museum and Vermont Jazz Center are also within 3 mi (5 km).

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

89 Grand Summit Way, West Dover
3.3
of 5, from 3 reviews
3.0 out of 5.0

Set amidst the mountains, this ski-in/ski-out resort in West Dover is within 6 mi (10 km) of Mount Snow and Mount Snow Golf Course and close to winter sports such as snowmobiling. Jacksonville Pond is 14.6 mi (23.5 km) away.

$109
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

401 Winchester St, Keene
3.9
of 5, from 212 reviews
3.0 out of 5.0

This family-friendly Keene hotel is located in the suburbs, within 1 mi (2 km) of Thorne-Sagendorph Art Gallery, Cheshire Children's Museum, and Historical Society of Cheshire County. Colonial Theatre and Horatio Colony Museum are also within 1 mi (2 km).

$84
Days Inn Keene NH

Days Inn Keene NH

3 Ash Brook Road, Keene
3.5
of 5, from 96 reviews
2.0 out of 5.0

Situated in Keene, this hotel is within 2 mi (3 km) of Cheshire Children's Museum, Thorne-Sagendorph Art Gallery, and Alumni Field. Horatio Colony Museum and Historical Society of Cheshire County are also within 2 mi (3 km).

$57
Super 8 Brattleboro

Super 8 Brattleboro

1043 Putney Road, Brattleboro
3.2
of 5, from 138 reviews
2.0 out of 5.0

Situated in Brattleboro, this motel is 0.4 mi (0.7 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro Museum & Art Center. Madame Sherri Forest and Estey Organ Museum are also within 3 mi (5 km).

$50
Motel 6 Brattleboro

Motel 6 Brattleboro

1254 Putney Rd, Brattleboro
2.9
of 5, from 71 reviews
2.0 out of 5.0

Situated in Brattleboro, this motel is 0.5 mi (0.8 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro Museum & Art Center. Madame Sherris Castle Ruins and Madame Sherri Forest are also within 3 mi (5 km).

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