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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $800, price is now $608 per person
$608
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,229, price is now $895 per person
$895
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,297, price is now $1,000 per person
$1,000
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $994, price is now $818 per person
$818
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free buffet breakfast each morning. A garden is also provided.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $841, price is now $715 per person
$715
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
This bed & breakfast features free WiFi in public areas, barbecue grills, and free self parking. A free bus station shuttle is offered as well. A 24-hour business center, a garden, and a lobby fireplace are also on offer.

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
The price is $81 total per night
$81 total
per night
Oct 14 - Oct 15
A garden is available at this campground.
Pet friendly
Free WiFi
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
The price is $109 total per night
$109 total
per night
Nov 1 - Nov 2
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
The price is $161 total per night
$161 total
per night
Nov 1 - Nov 2
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
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
The price is $156 total per night
$156 total
per night
Nov 2 - Nov 3
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.
Pet friendly
Parking included
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
The price is $154 total per night
$154 total
per night
Nov 1 - Nov 2
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
The price is $111 total per night
$111 total
per night
Nov 1 - Nov 2
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?
$608 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.