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.
Colonial Motel

Colonial Motel

3 out of 5
Price was $809, price is now $781 per person
$781
per person
Nov 13 - Nov 20
found 1 hour ago
Roundtrip non-stop flight included
Sacramento (SMF) to Springfield (VSF)
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 garden, a grocery/convenience store, and a lobby fireplace are also on offer.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $1,049, price is now $911 per person
$911
per person
Nov 13 - Nov 20
found 1 hour ago
Roundtrip non-stop flight included
Sacramento (SMF) to Springfield (VSF)
This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the gym and perks like free WiFi and a free area shuttle. You'll appreciate the sauna, bar/lounge, and laundry facilities.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $874, price is now $818 per person
$818
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Springfield (VSF)
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast and free WiFi. A garden and a picnic area are also provided.
Doveberry Inn

Doveberry Inn

3 out of 5
Price was $934, price is now $882 per person
$882
per person
Nov 13 - Nov 20
found 1 hour ago
Roundtrip non-stop flight included
Sacramento (SMF) to Springfield (VSF)
This bed & breakfast doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A virtual front desk are provided for your convenience.
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
Price was $1,021, price is now $988 per person
$988
per person
Nov 13 - Nov 20
found 1 hour ago
Roundtrip non-stop flight included
Sacramento (SMF) to Springfield (VSF)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Top Winchester hotels deals

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups

Winchester NH
$75 nightly
The price is $81 total per night
$81 total
Oct 15 - Oct 16
Total with taxes and fees
A garden is available at this campground.
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $109 total per night
$109 total
Nov 1 - Nov 2
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 garden, a grocery/convenience store, and a lobby fireplace are also on offer.
Breakfast included
Pet friendly
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $161 total per night
$161 total
Nov 1 - Nov 2
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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $154 total per night
$154 total
Nov 2 - Nov 3
Total with taxes and fees
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.
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
$142 nightly
The price is $154 total per night
$154 total
Nov 1 - Nov 2
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
Gardner Inn

Gardner Inn

2 out of 5
22 Pearson Blvd Gardner MA
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $119 total per night
$119 total
Nov 1 - Nov 2
Total with taxes and fees
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Pet friendly
Parking 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.

Stay near popular Winchester attractions

Winchester Speedpark

You can take time to visit Winchester Speedpark during your travels to Winchester. While you're in the area, stroll along the lakeside.
See properties

Frequently asked questions

How much are vacation packages to Winchester?
$781 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

A snow-covered town with a river running through it, surrounded by mountains and trees.
A snow-covered bridge over a river with a red roof, surrounded by trees and buildings.
A wooden pedestrian bridge with a lattice roof structure.
A covered bridge with a sign reading "Ashuelot Covered Bridge 1864" and a warning about the fine for riding or driving over it.