Winchester Vacations

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Find the Best Winchester Vacation Packages

Winchester Hotel Deals

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,000 reviews)
Friendly staff, clean room, gym and poll area.

Reviewed on 4 February 2026

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The Colonial Hotel
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is AED 452 per night from Mar 5 to Mar 6
AED 452
AED 497 total
5 Mar - 6 Mar
includes taxes & fees
8.4/10 Very Good! (760 reviews)
Nice location… clean room! Breakfast was not appetizing…

Reviewed on 29 January 2026

Comfort Inn & Suites Brattleboro I-91
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is AED 419 per night from Mar 1 to Mar 2
AED 419
AED 461 total
1 Mar - 2 Mar
includes taxes & fees
8.2/10 Very Good! (941 reviews)
The room was very clean, and the showers hot water was amazing! The staff was friendly and would let us know when breakfast was available so we wouldn’t miss it ! Robert and Destiny always had a smile on their face and greeted us when we arrived and when we left the hotel. I would definitely stay ...

Reviewed on 9 February 2026

Hampton Inn Brattleboro
See all 465 properties in Winchester
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.

Frequently asked questions

How do I find cheap flights to Winchester that have flexible change policies?
When it comes to flying these days, flexibility is essential. That's why we've added a "No change fee" filter to help you track down flexible, cheap tickets to Winchester. It's on the left-hand side of your screen under the "Flexible change policies" heading.
Which airlines fly to Winchester?
Take your pick of a good selection of airlines that fly into or near Winchester. These are a few of the best:

  • Delta Air Lines - 3,883 flights to or near Winchester each month, including 3,701 flights to Logan Intl. Airport (BOS) and 182 to Bradley Intl. Airport (BDL) per month.
  • JetBlue Airways - 3,559 flights to or near Winchester each month, including 3,407 flights to Logan Intl. Airport (BOS) and 151 to Bradley Intl. Airport (BDL) per month.
  • American Airlines - 2,717 flights to or near Winchester each month, including 2,106 flights to Logan Intl. Airport (BOS) and 611 to Bradley Intl. Airport (BDL) per month.

How can I find cheap tickets to Winchester?
An excellent strategy for scoring cheap fares is to be flexible with your travel dates. Begin with searching for your flight to Winchester, then click on the "flexible dates" box to compare prices for nearby days. Another good tip? Book well ahead of time. For an idea of fares, was the lowest price for a flight to Winchester in the last seven days.
How much is a flight to Winchester?
If you were traveling one way from (), you could've picked up a bargain fare for in the last seven days. Round-trip flights to Winchester ranged from to during this same period.
What are the most popular airports to fly into in Winchester?
When it comes to selecting which Winchester airport to land at, these are your options:

  • Logan Intl. Airport (BOS) - 12,948 flights per month.
  • Bradley Intl. Airport (BDL) - 1,911 flights per month.

When is the cheapest time to fly to Winchester?
Jetting off on a Tuesday, followed by a Monday, is generally the best way to nab the cheapest deal. Avoid weekends if possible, because Saturday is typically the most expensive day. Spend the money you saved having a good time in Winchester instead!
How much is a plane ticket to Winchester?
Prices varied from to over the last seven days. When you're ready to book, we'll help you pick up a cheap flight to Winchester.
What months are the cheapest to book a flight to Winchester?
To secure a fabulous deal to Winchester, try to book during the month of February when the price of fares are at their lowest. When's the most expensive? In the United States, it's the festive month of December.
How long is a flight to Winchester?
It could take you an hour or two or longer — it really depends on which part of the USA you're journeying from. The average flight times for these busy domestic routes to Winchester will give you some idea of what you can expect:

  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 48 minutes
  • New York, NY (LGA-LaGuardia) to Logan Intl. Airport (BOS) - 1 hour and 35 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Logan Intl. Airport (BOS) - 1 hour and 25 minutes