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.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $543, price is now $425 per person
$425
per person
Mar 25 - Mar 28
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $590, price is now $509 per person
$509
per person
Mar 25 - Mar 28
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $914, price is now $839 per person
$839
per person
Mar 25 - Mar 28
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $515, price is now $474 per person
$474
per person
Mar 25 - Mar 28
found 15 hours ago
Roundtrip flight included
Orlando (MCO) 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.

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
Jan 19 - Jan 20
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
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$124 nightly
The price is $137 total per night
$137 total
Jan 29 - Jan 30
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
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $93 total per night
$93 total
Jan 15 - Jan 16
Total with taxes and fees
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Parking included
Free WiFi
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
$200 nightly
The price is $219 total per night
$219 total
Feb 5 - Feb 6
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
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $161 total per night
$161 total
Jan 20 - Jan 21
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
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $103 total per night
$103 total
Jan 26 - Jan 27
Total with taxes and fees
Free self parking is available and the motel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A picnic area is also provided.
Breakfast included
Pet friendly
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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

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

Bennett Gorge

You can take time to visit Bennett Gorge during your travels to Richmond.

Bennett Gorge

Cass Pond

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

Cass Pond

Frequently asked questions

How much are vacation packages to Winchester?
$425 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

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.
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.