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 ...
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 ...
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 ...
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. ...
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 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 & 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 ...
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
Stay at this 3-star business-friendly hotel in Keene. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road, Keene, NH
17.88 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 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 ...
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 ...
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 ...
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 ...
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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.

American Airlines
Fri, Sep 12 - Tue, Sep 16
PDX
Portland Intl.
BOS
Logan Intl.
$163 Roundtrip, found 6 days ago
$163
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Sep 12 from Portland Intl. to Logan Intl., returning Tue, Sep 16, priced at $163 found 6 days ago
Spirit Airlines
Tue, Aug 19 - Sun, Aug 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$196 Roundtrip, found 3 days ago
$196
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Aug 19 from Los Angeles Intl. to Logan Intl., returning Sun, Aug 31, priced at $196 found 3 days ago
JetBlue Airways
Sun, Aug 31 - Mon, Sep 1
PDX
Portland Intl.
BOS
Logan Intl.
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Aug 31 from Portland Intl. to Logan Intl., returning Mon, Sep 1, priced at $207 found 1 day ago
United
Wed, Sep 24 - Fri, Sep 26
LAX
Los Angeles Intl.
BOS
Logan Intl.
$221 Roundtrip, found 5 days ago
$221
Roundtrip
found 5 days ago
Select United flight, departing Wed, Sep 24 from Los Angeles Intl. to Logan Intl., returning Fri, Sep 26, priced at $221 found 5 days ago
Delta
Sat, Oct 4 - Sat, Oct 18
PDX
Portland Intl.
BOS
Logan Intl.
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 4 from Portland Intl. to Logan Intl., returning Sat, Oct 18, priced at $247 found 1 day ago