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
Stay at this 3-star business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
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 ...
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 ...
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
18.53 km from city center
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
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. ...
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. ...
Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

2.5 out of 5
1254 Putney Rd, Brattleboro, VT
18.98 km from city center
Stay at this motel in Brattleboro. Enjoy free WiFi, free parking, and room service. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl ...
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
18 km from city center
Stay at this 3-star 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 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 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 ...
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 out of 5
20 Riverside Drive, West Chesterfield, NH
18.35 km from city center
Book a stay at this business-friendly hotel in West Chesterfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise 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 ...
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 ...
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 ...
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive, Guilford, VT
18.58 km from city center
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions ...
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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
Wed, Sep 2 - Tue, Sep 8
PDX
Portland Intl.
BOS
Logan Intl.
$183 Roundtrip, found 5 days ago
$183
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Sep 2 from Portland Intl. to Logan Intl., returning Tue, Sep 8, priced at $183 found 5 days ago
Alaska Airlines
Wed, Sep 2 - Tue, Sep 8
PDX
Portland Intl.
BOS
Logan Intl.
$253 Roundtrip, found 5 days ago
$253
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Sep 2 from Portland Intl. to Logan Intl., returning Tue, Sep 8, priced at $253 found 5 days ago
American Airlines
Wed, Sep 2 - Tue, Sep 8
PDX
Portland Intl.
BOS
Logan Intl.
$258 Roundtrip, found 5 days ago
$258
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Sep 2 from Portland Intl. to Logan Intl., returning Tue, Sep 8, priced at $258 found 5 days ago
United
Wed, Sep 2 - Tue, Sep 8
PDX
Portland Intl.
BOS
Logan Intl.
$268 Roundtrip, found 5 days ago
$268
Roundtrip
found 5 days ago
Select United flight, departing Wed, Sep 2 from Portland Intl. to Logan Intl., returning Tue, Sep 8, priced at $268 found 5 days ago