A group of hikers on rocky terrain with dense forest in the background.
Photo by Stephen Leonardi
Open Photo by Stephen Leonardi

Jaffrey Vacations from $296

Book a Hotel + Flight or Car together to unlock savings

Your Jaffrey Vacation

When you book a Jaffrey vacation package, it's all about letting go and enjoying your adventure to the fullest. Discover the best things about this lively city knowing that everything has been organized in advance. If your trip to Jaffrey includes a little sightseeing, hit up popular attractions like Monadnock State Park, Shattuck Golf Course and Cathedral of the Pines. Browse Expedia's extensive range of travel options and book your perfect vacation to Jaffrey today.

The Latest Jaffrey Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 11 - Dec 13

    Stonybrook Motel & Lodge + Flight

    Franconia
    2 nights
    2.0 star property
    7.6/10 - Good (1,002 reviews)
    Roundtrip • Miami (MIA) - Manchester (MHT)
    MIA - BOS • Nonstop BOS - FLL • Nonstop
    $417
    $296
    per traveler
    found 1 day ago
    Stonybrook Motel & Lodge
  • Dec 11 - Dec 13

    The Sunny G B&B + Flight

    Campton
    2 nights
    2.5 star property
    9.4/10 - Exceptional (728 reviews)
    "We booked the Sunny B for a fall getaway, excited to experience our first bed and breakfast and enjoy the beauty of the season. Unfortunately, we were disappointed to learn upon arrival that breakfast was not included because we had booked a discounted rate. This was never mentioned in the listing or disclosed during booking. When you book a bed and breakfast, you naturally expect both a bed and breakfast. Had we known, we would have booked somewhere else. Another inconvenience was running out..."
    Reviewed November 10, 2026
    Roundtrip • Miami (MIA) - Manchester (MHT)
    MIA - BOS • Nonstop BOS - FLL • Nonstop
    $423
    $306
    per traveler
    found 1 day ago
    The Sunny G B&B
  • Dec 19 - Dec 23

    The Village of Loon Mountain Fixed Rooms + Flight

    Lincoln
    4 nights
    2.0 star property
    8.6/10 - Excellent (73 reviews)
    "Check-in process was worse . We had late check-in . No one was there at the counter. The phone which was supposed to give the code to get the key was not working. We waited there for more than 3 hours in the cold till 11:30 pm. I would not recommend this place ."
    Reviewed October 30, 2026
    Roundtrip • Chicago (ORD) - Manchester (MHT)
    ORD - MHT • 1 stop MHT - ORD • 1 stop
    $1,116
    $834
    per traveler
    found 12 hours ago
    The Village of Loon Mountain Fixed Rooms
  • Dec 19 - Dec 23

    The Village of Loon Mountain + Flight

    Lincoln
    4 nights
    3.0 star property
    8.6/10 - Excellent (634 reviews)
    "This was a perfect location and just the right fit for us to relax in a quiet atmosphere. Mariah was absolutely wonderful."
    Reviewed November 6, 2026
    Roundtrip • Chicago (ORD) - Manchester (MHT)
    ORD - MHT • 1 stop MHT - ORD • 1 stop
    $961
    $767
    per traveler
    found 12 hours ago
    The Village of Loon Mountain
  • Dec 11 - Dec 13

    Presidential Mountain Resort + Flight

    Bethlehem
    2 nights
    3.0 star property
    9.6/10 - Exceptional (338 reviews)
    Roundtrip • Miami (MIA) - Manchester (MHT)
    MIA - BOS • Nonstop BOS - FLL • Nonstop
    $566
    $468
    per traveler
    found 1 day ago
    Presidential Mountain Resort

Where to stay near Jaffrey

Jaffrey, New Hampshire, is a perfect getaway destination for outdoor enthusiasts and families seeking adventure. Explore the scenic Jaffrey Center and uncover hidden gems along Northfield Rd. Enjoy a blend of relaxation and adventure in this charming locale, ideal for creating lasting memories.

Winchendon

For travelers seeking a memorable trip, Winchendon offers a charming blend of family-friendly activities and natural beauty. Just a short distance from Jaffrey, this city invites visitors to explore its scenic landscapes, including the picturesque Paradise Island and the nearby lake and beach. With attractions like The Winchendon School and the historic Winchendon Town Hall, guests can enjoy a mix of education and history. Winchendon is an excellent choice for accommodation, providing a perfect base for outdoor adventures and romantic getaways.

Rindge

Experience the charm of Rindge, an excellent hub for travelers seeking a family-friendly getaway surrounded by nature. This lovely city offers access to beautiful outdoor scenery, with attractions like Contoocook Lake for relaxing days by the water, Franklin Pierce University for a taste of local culture, and the serene Cathedral of the Pines for moments of reflection. Located about 4 miles from Jaffrey, Rindge is a smart choice for accommodations, ensuring you’re close to all the excitement while enjoying a peaceful retreat.

Peterborough

Make your vacation planning effortless by staying in Peterborough, a haven for family and outdoor enthusiasts thanks to its stunning scenery and adventure opportunities. Visitors will enjoy exploring the breathtaking Pack Monadnock Mountain and the serene Monadnock State Park, while the historic Peterborough Town House adds a cultural touch to your experience. Located about 6 miles by car from Jaffrey, Peterborough makes for a smart choice for your stay, combining natural beauty with accessible attractions.

Sharon

Sharon stands out as a prime spot for families and nature enthusiasts interested in a weekend getaway. Nestled about 5 miles from Jaffrey, this charming village offers easy access to stunning attractions like Pack Monadnock Mountain and the serene beaches nearby. Visitors can enjoy educational experiences at the Cathedral of the Pines and explore the historic Temple Town Hall. With its inviting atmosphere year-round, Sharon is a smart choice for those seeking outdoor adventures and memorable family experiences.

Fitzwilliam

Travelers seeking a weekend getaway will find Fitzwilliam to be the ideal base for their vacation, featuring stunning natural scenery and a range of outdoor activities. With attractions like Monadnock State Park and Laurel Lake nearby, visitors can enjoy hiking, skiing, and relaxing by the water. Fitzwilliam is just about a 6-mile drive from Jaffrey, making it a convenient spot for families and nature lovers alike. Booking a stay in Fitzwilliam ensures an enriching and memorable experience in the heart of New Hampshire.

Discover the most popular places to visit in Jaffrey

Jaffrey Hotel Deals

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

What's the best vacation package for Jaffrey?

A Jaffrey vacation package for couples seeking a romantic getaway could center on a stay at Monadnock Inn, rated 7.8 out of 10. This charming inn offers free breakfast and a kitchen, providing a comfortable base for exploring the scenic outdoor surroundings. Travelers frequently praise its great location, which is about 2 miles from Monadnock State Park, and its great facilities, making it ideal for a peaceful escape.


For those seeking the best vacation packages in Jaffrey that offer great value or are family-friendly, a package with a stay at Monadnock Inn is a solid choice. With free breakfast and a kitchen, it helps keep costs down and provides convenience for families. Its location, about 2 miles from Contoocook Lake and Monadnock State Park, is highlighted by travelers as great for outdoor activities.

How can I save money on a Jaffrey vacation package?

When you bundle, you can save up to 30%*. To save money on a Jaffrey package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What are the top things to do in Jaffrey?

Jaffrey, an outdoor and nature destination, offers a variety of activities centered around its scenic landscapes and recreational areas:


Browse and book things to do in Jaffrey on Expedia.

Do you need to rent a car in Jaffrey, or is public transport enough?

For a Jaffrey vacation, a rental car is highly recommended to fully explore this outdoor and nature destination. Attractions like Monadnock State Park, about 7 miles from central Jaffrey, and Wachusett Mountain Ski Area, about 19 miles away, are spread out, making a car essential for flexible travel. While some local points of interest like Jaffrey Civic Center are within about a 5-minute walk of the center, reaching the wider natural areas and lakes requires personal transportation.


Boston Logan International Airport (BOS) is about 62 miles away, and Manchester-Boston Regional Airport (MHT) is also a common entry point, making a car rental practical for reaching Jaffrey and exploring the surrounding region as part of your Jaffrey vacation packages with flights.

Are Jaffrey vacation package hotels conveniently located?

Jaffrey's vacation package hotels are generally well-situated for exploring the area's natural beauty. For example, Monadnock Inn, rated 7.8 out of 10, is about 2 miles from central Jaffrey and also about 2 miles from Monadnock State Park. This property offers free breakfast, free WiFi, and a kitchen, making it a comfortable base for outdoor adventures. Staying at a hotel like this allows easy access to both the town and nearby natural attractions, enhancing your Jaffrey vacation package experience.

Can I change or cancel my Jaffrey vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Jaffrey vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Jaffrey vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Jaffrey vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Jaffrey?

To find last-minute vacation packages to Jaffrey, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Jaffrey vacation packages?

Free cancellation on a Jaffrey vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Jaffrey vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Jaffrey getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Jaffrey vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.