Winchester Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

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 ...
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. ...
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 ...
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. ...
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 ...
Gardner Inn

Gardner Inn

2 out of 5
22 Pearson Blvd Gardner MA
40.24 km from city center
Stay at this hotel in Gardner. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Dunn State Park and 1761 Old Mill Gift Shop are located ...
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 ...
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 ...
Econo Lodge Brattleboro South

Econo Lodge Brattleboro South

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 ...
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 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 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 ...
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. ...
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 ...
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.

United
Wed, Sep 16 - Sat, Sep 26
PDX
Portland Intl.
BOS
Logan Intl.
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select United flight, departing Wed, Sep 16 from Portland Intl. to Logan Intl., returning Sat, Sep 26, priced at $237 found 3 days ago
JetBlue Airways
Wed, Sep 16 - Thu, Sep 17
LAX
Los Angeles Intl.
BOS
Logan Intl.
$242 Roundtrip, found 2 days ago
$242
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Sep 16 from Los Angeles Intl. to Logan Intl., returning Thu, Sep 17, priced at $242 found 2 days ago
American Airlines
Wed, Sep 23 - Wed, Sep 30
LAX
Los Angeles Intl.
BOS
Logan Intl.
$247 Roundtrip, found 2 days ago
$247
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Sep 23 from Los Angeles Intl. to Logan Intl., returning Wed, Sep 30, priced at $247 found 2 days ago
Delta
Tue, Sep 22 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$252 Roundtrip, found 2 days ago
$252
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 22 from Los Angeles Intl. to Logan Intl., returning Wed, Sep 23, priced at $252 found 2 days ago
Southwest Airlines
Tue, Sep 22 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$267 Roundtrip, found 2 days ago
$267
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Sep 22 from Los Angeles Intl. to Logan Intl., returning Wed, Sep 23, priced at $267 found 2 days ago