Deals on vacations and trips to Winchester

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Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Deerhill Inn

Deerhill Inn

3.5 out of 5
Price was $680, price is now $673 per person
$673
per person
Jun 5 - Jun 7
found 11 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Springfield (VSF)
This bed & breakfast features a seasonal outdoor pool and a bar/lounge. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A terrace, a garden, and a library are also on offer.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $930, price is now $813 per person
$813
per person
May 15 - May 17
found 8 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Springfield (VSF)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and luggage storage are also offered on site.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $834, price is now $735 per person
$735
per person
May 15 - May 17
found 8 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Springfield (VSF)
Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi in public areas and an area shuttle. You'll appreciate the outdoor pool, bar/lounge, and laundry facilities.
Windham Hill Inn

Windham Hill Inn

4 out of 5
Price was $923, price is now $817 per person
$817
per person
May 15 - May 17
found 6 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Springfield (VSF)
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. WiFi in public areas is free. A garden is also provided.
Chalet 239

Chalet 239

2 out of 5
Price was $834, price is now $739 per person
$739
per person
May 15 - May 17
found 6 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Springfield (VSF)
The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. A picnic area and a virtual front desk are also provided.

Top Winchester hotels deals

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Free Cancellation
Reserve now, pay when you stay
$160 nightly
The price is $179 total per night
$179 total
Mar 18 - Mar 19
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$100 nightly
The price is $110 total per night
$110 total
Mar 18 - Mar 19
Total with taxes and fees
This smoke-free motel features a full-service spa, 2 indoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $143 total per night
$143 total
Mar 23 - Mar 24
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
Pool
Hot Tub
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Free Cancellation
$124 nightly
The price is $136 total per night
$136 total
Mar 28 - Mar 29
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
$182 nightly
The price is $199 total per night
$199 total
Mar 18 - Mar 19
Total with taxes and fees
A rooftop terrace is featured at this hotel, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also on offer.
Parking included
Free WiFi
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $129 total per night
$129 total
Mar 18 - Mar 19
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
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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.

Popular places to visit

Cass Pond

Commune with nature and explore the great outdoors at Cass Pond during your travels in Richmond.

Cass Pond

Barden State Wildlife Management Area

Explore the great outdoors at Barden State Wildlife Management Area, a lovely green space in Richmond.

Barden State Wildlife Management Area

New England Sweetwater Farm & Distillery

You can take time to visit New England Sweetwater Farm & Distillery during your travels to Winchester. While you're in the area, stroll along the lakeside.

New England Sweetwater Farm & Distillery

Frequently asked questions

How much are vacation packages to Winchester?
$673 is all you need to spend for a wonderful vacation in Winchester. Bundle your flights and hotel into a vacation package with Travelocity and see the savings start to add up. With prices this good, it's never been more tempting to travel.
How long should my Winchester vacation be?
Many visitors like to spend around 3 nights in Winchester. But what works for them mightn't work for you. Whether you prefer to stay for a few days or a few weeks, you'll enjoy discovering all the amazing things that this destination has to offer.
Where can I get the best vacation package deals for Winchester?
Travelocity has endless ways to score a sensational Winchester package deal. Select from 400 partner airlines and 1,000,000 properties all over the globe and craft a travel itinerary that fits your style. With this amount of choice at your fingertips, it's easy to plan your next big adventure.
Why should I purchase my Winchester vacation bundle via Travelocity?
From our 24/7 support to our range of exhilarating destinations, we're dedicated to fulfilling your vacation dreams. All you'll have to do is to click and book — our Price Match Guarantee will make sure you get the cheapest price.
Will I save money on my Winchester car rental if I book it with a hotel or flight?
With a Winchester vacation package, you can combine your hotel, flight and car bookings and save a whole lot. If you're eager to uncover the best of this exciting area, why not make tracks to Fenway Park? This popular attraction is 70 mi from Winchester. With your own set of wheels, you'll be there in a flash.
Which airport is best for Winchester?
Bradley Intl. Airport (BDL) (60 mi away from the downtown area), Manchester-Boston Regional Airport (MHT) (50 mi away from central Winchester) and Lebanon Municipal Airport (LEB) (60 mi away from central Winchester) are the best options for Winchester.
Where should I stay when visiting Winchester?
Many people opt to check in to the Story Book Lake Front Chateau with Private Beach!. It's a terrific base for your Winchester getaway.

Photos of local treasures

Browse Winchester vacation photos for more inspiration

Winchester, New Hampshire in winter
covered bridge in winter -Ashuelot Covered Bridge, Winchester, New Hampshire
Black and white Lattice work detail on The Ashuelot Covered Bridge crosses the Ashuelot River and Bolton Road in Winchester New Hampshire
The Ashuelot Covered Bridge is a historic wooden covered bridge over the Ashuelot River on Bolton Road, just south of its intersection with NH 119 in Ashuelot, New Hampshire, an unincorporated village of Winchester.