Londonderry Vacations from $331
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Your Londonderry Vacation
From its rich history to its cultural experiences and beyond, there's loads to like about Londonderry. Uncover the delights of this exciting city with a Londonderry vacation package that's customized for you. Like to explore your surroundings? Magic Mountain Ski Resort, Jamaica State Park and Viking Nordic Center are a few of the leading places to visit during a trip to Londonderry. Check out Expedia's wide range of travel options and start planning your dream vacation to Londonderry now.
The Latest Londonderry Vacation Packages
- Bentley House Bed and Breakfast
Jan 21 - Jan 24Bentley House Bed and Breakfast + Flight
Poultney3 nights2.0 star property10/10 - Exceptional (44 reviews)Roundtrip • Boston (BOS) - Rutland (RUT)BOS - RUT • Nonstop RUT - BOS • Nonstop$426$331found 1 day agoper traveler - The Suites at Killington Center
Jan 21 - Jan 24The Suites at Killington Center + Flight
Killington3 nights3.5 star propertyRoundtrip • Boston (BOS) - Rutland (RUT)BOS - RUT • Nonstop RUT - BOS • Nonstop$1,598$1,134found 1 day agoper traveler - Pointe at Castle Hill Resort
Jan 21 - Jan 24Pointe at Castle Hill Resort + Flight
Cavendish3 nights3.5 star property8.8/10 - Excellent (1,000 reviews)Roundtrip • Boston (BOS) - Rutland (RUT)BOS - RUT • Nonstop RUT - BOS • Nonstop$646$486found 1 day agoper traveler - Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Dec 25 - Dec 31Holiday Inn Club Vacations Mount Ascutney Resort by IHG + Flight
Brownsville6 nights3.0 star property9.0/10 - Wonderful (898 reviews)Roundtrip • Boston (BOS) - Rutland (RUT)BOS - LEB • Nonstop LEB - BOS • Nonstop$1,205$922found 17 hours agoper traveler - The Vermont Inn
Jan 21 - Jan 24The Vermont Inn + Flight
Rutland3 nights3.0 star property9.0/10 - Wonderful (441 reviews)"Our room was large and comfortable, with a large, well-supplied bathroom. The fellow at the front desk was friendly and helpful. It feels like a very nice rural country inn. There isn't a lot else there, as there aren't 24-hour onsite staff or a fitness room or many other lobby amenities. I wouldn't hesitate to come back."Reviewed October 15, 2026Roundtrip • Boston (BOS) - Rutland (RUT)BOS - RUT • Nonstop RUT - BOS • Nonstop$728$588found 1 day agoper traveler
Where to stay near Londonderry
Ludlow
Discover Ludlow, a fantastic destination for outdoor enthusiasts and families seeking adventure and relaxation. With its stunning natural beauty, Ludlow offers access to activities like skiing at nearby resorts and exploring scenic spots such as Lake Rescue and Buttermilk Falls. Just about a 16-mile drive from Londonderry, Ludlow serves as an ideal base for your Vermont getaway, making it a smart choice for travelers looking to enjoy a mix of sports and nature.
Stratton
Experience the charm of Stratton, an excellent hub for families and outdoor enthusiasts eager to enjoy activities like skiing, hiking, and exploring the stunning Green Mountain National Forest. With attractions such as the historic Hildene and the picturesque Winhall River nearby, visitors can immerse themselves in nature and history alike. Located about 15 miles by car from Londonderry, Stratton offers a smart choice for those seeking a memorable getaway with easy access to Vermont's natural beauty.
Peru
Make your vacation planning effortless by staying in Peru, Vermont, a haven for outdoor enthusiasts and families due to its proximity to thrilling activities like skiing at local resorts and exploring the beautiful Emerald Lake State Park. Visitors can also enjoy the Vermont Summer Festival and the scenic landscapes of nearby mountains. Located about 5 miles by car from Londonderry, Peru is a smart choice for a memorable getaway in all seasons.
South Londonderry
South Londonderry stands out as a prime spot for outdoor enthusiasts and families interested in exploring Vermont's natural beauty. With attractions like Jamaica State Park and the serene Winhall River, visitors can immerse themselves in a variety of activities year-round, from skiing in winter to hiking in summer. Located about 4 miles from Londonderry, South Londonderry offers easy access to the Stratton Tennis School and stunning landscapes. Choosing South Londonderry ensures a memorable stay amidst Vermont's charm.
Weston
Travelers seeking a weekend getaway or family adventure will find Weston to be the ideal base for their vacation, featuring stunning outdoor experiences year-round. With attractions like the serene Lowell Lake State Park and the tranquil West River, visitors can immerse themselves in nature. Just about a 5-mile drive from Londonderry, Weston provides easy access to ski resorts and other sports activities, making it a smart choice for those looking to enjoy Vermont's beautiful landscapes.
Discover the most popular places to visit in Londonderry
Londonderry Hotel Deals
The Upper Pass Lodge at Magic Mountain
The Upper Pass Lodge at Magic Mountain
"The Inn is in a beautiful setting. The staff were very friendly and helpful. My room was spacious and a comfortable arm chair and good lamp provided a cozy place for R&R. The spacious common area & well kept grounds would be a very pleasant place to spend time with family and friends. I was advised in advance that the restaurant was not serving dinner, but the staff provided a list of eateries in the local area. I had a very good meal at the New American Grill. The breakfast menu at the...
Blue Gentian Lodge at Magic Mountain
Blue Gentian Lodge at Magic Mountain
Sun Lodge near Manchester VT, Ascend Collection Hotel
Sun Lodge near Manchester VT, Ascend Collection Hotel"The people at the front desk were extremely friendly and helpful."
Hampton Inn and Suites Manchester
Hampton Inn and Suites Manchester"A"
Frequently Asked Questions
How much does a Londonderry vacation package cost?
Offering excellent value package deals from $331 on Expedia, you'll be surprised at how little a vacation to Londonderry costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Londonderry?
If you'd like to score a cheap Londonderry vacation package, consider traveling in February, April and May. You'll generally find better rates on hotels and flights during these months — ideal for a budget-friendly break.
How many days is enough for Londonderry?
Generally, a handful of days is enough to see the major attractions during your Londonderry vacation. However, if you prefer to have some time to chill out or take day trips, consider extending your trip.
Is it worth booking a vacation package to Londonderry?
Londonderry is a good vacation destination with attractions like Magic Mountain Ski Resort among the many things to keep you entertained. Whether you're traveling with the family or planning a trip with friends, a Londonderry vacation promises a good time for everyone.
How to find the best Londonderry package deals?
Use Expedia's filters to find some terrific Londonderry package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Londonderry package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Londonderry vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights separately. Better still, you can personalize your Londonderry trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Londonderry?
If you're considering a spontaneous Londonderry adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Londonderry vacation packages?
Your Londonderry trip is meant to be an escape from your daily routine, not a source of money worries. So to give you more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.