Winchester Vacations

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Top Hotel Deals

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
42.31 km from city center
Book a stay at this business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd Greenfield MA
28.52 km from city center
Book a stay at this business-friendly hotel in Greenfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
18.68 km from city center
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
19.03 km from city center
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
18.95 km from city center
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
18.3 km from city center
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
18.21 km from city center
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free parking, and room service. Our guests praise the breakfast and the helpful staff ...
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
18 km from city center
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
23.92 km from city center
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
16.67 km from city center
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Inn At Crumpin Fox

The Inn At Crumpin Fox

2.5 out of 5
71 Northfield Rd Bernardston MA
17.18 km from city center
Book a stay at this business-friendly hotel in Bernardston. Enjoy free WiFi, free parking, and a conference center. Our guests praise the helpful staff and the ...
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
100 Chickering Drive Brattleboro VT
18.8 km from city center
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St Keene NH
19.73 km from city center
Book a stay at this business-friendly hotel in Keene. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 out of 5
80 Concord Street Peterborough NH
37.73 km from city center
Stay at this hotel in Peterborough. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Mariposa ...
Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
515 Canal St Brattleboro VT
16.53 km from city center
Stay at this motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Vermont Marketplace and Estey Organ Museum are located ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Sep 12 - Sun, Sep 13
PDX
Portland Intl.
BOS
Logan Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Sep 12 from Portland Intl. to Logan Intl., returning Sun, Sep 13, priced at $197 found 3 days ago
Breeze Airways
Tue, Dec 30 - Wed, Jan 7
LAX
Los Angeles Intl.
PVD
T.F. Green
$289 Roundtrip, found 6 days ago
$289
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Tue, Dec 30 from Los Angeles Intl. to T.F. Green, returning Wed, Jan 7, priced at $289 found 6 days ago
United
Sat, Sep 12 - Sun, Sep 13
PDX
Portland Intl.
BOS
Logan Intl.
$302 Roundtrip, found 3 days ago
$302
Roundtrip
found 3 days ago
Select United flight, departing Sat, Sep 12 from Portland Intl. to Logan Intl., returning Sun, Sep 13, priced at $302 found 3 days ago
American Airlines
Tue, Dec 30 - Wed, Jan 7
LAX
Los Angeles Intl.
PVD
T.F. Green
$305 Roundtrip, found 6 days ago
$305
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Dec 30 from Los Angeles Intl. to T.F. Green, returning Wed, Jan 7, priced at $305 found 6 days ago
Alaska Airlines
Sat, Sep 12 - Sun, Sep 13
PDX
Portland Intl.
BOS
Logan Intl.
$307 Roundtrip, found 3 days ago
$307
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Sat, Sep 12 from Portland Intl. to Logan Intl., returning Sun, Sep 13, priced at $307 found 3 days ago