Holiday houses in Jaffrey

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Top-rated holiday rentals in Jaffrey

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A cozy living area features a vintage cupboard with glass doors displaying a variety of dishes and decor. A small table with a bouquet of flowers sits in front of a comfortable grey chair. Natural light fills the space through a window adorned with patterned curtains.
Home in Jaffrey
4.9 out of 5 average rating, 113 reviews

Laura's place re-done 2 bedrooms 2 bathrooms

This quaint 2 bedrooms newly redecorated / vintage style. Now has a king and a queen size bed, very comfortable. There are some cool 1950s pieces in the unit. Newly remodeled 1 bathroom. There are 2 bathrooms. Private entry/lockbox. washer and dryer. Jaffrey is at the base of Mount Monadnock, the most hiked mount climbed in North America. You can see the mountain as you walk downtown . There several beautiful historic homes in our area. There are several lakes to swim, kayak or fish.

Top Guest favourite
A quaint cabin sits amidst lush greenery, framed by tall trees. The blue exterior features a welcoming porch, flanked by blooming white hydrangeas. A well-kept lawn complements the serene landscape, providing a peaceful retreat in a natural setting.
Guesthouse in New Ipswich
4.95 out of 5 average rating, 428 reviews

"The Porch" Your cozy home away from home!

Welcome to The Porch! Ready for a mini vacation, or just a place to hang out, or work from? You are most welcome here! . This cozy cabin is very flexible and user friendly! It is private to only your group! The downstairs with all it offers, is for one or two person stays. The upstairs becomes available if you enter 3 or more people. This building is in the backyard of our home, as in photos on our Airbnb site, Other info is listed there also! Info book is in room! Welcome! (no pets)

Top Guest favourite
A modern dining area is presented with a light wood table accompanied by four matching chairs. A neutral-colored vase with greenery sits at the center of the table. The space is brightened by large windows and features a comfortable living room area in the background.
Home in Jaffrey
4.98 out of 5 average rating, 53 reviews

Squantum Place

Relax with the whole family at this peaceful place to stay. This brand new townhome has enough beds to sleep 9. It is within walking distance to 344 acre Lake Contoocook, and close to trails and popular hikes. Mount Monadnock, one of the most hiked mountains in world, is only 10 minutes away. Modern comforts include WiFi, smart TV’s, designated work space, fully stocked kitchen and laundry. Primary bedroom and full bathroom on the main level. Enjoy the comforts of A/C throughout this home!

Top Guest favourite
A three-story home is viewed from the driveway, featuring a combination of siding and shingles. A wooden deck extends from the second floor, while a garage door and entrance are visible on the first floor. Surrounding foliage offers a natural backdrop.
Home in Jaffrey
4.89 out of 5 average rating, 108 reviews

Cozy New England Getaway | Minutes to Monadnock

Where cozy wilderness intertwines, in the heart of nature. Your exclusive 3BR/3BA lodge sitting on secluded acres in Jaffrey, NH awaits you- complete with tranquil pond, two serene decks and two spacious living room areas to gather. 10 Minutes from Mount Monadnock, adventure by day and indulge in comfort by night. Chef's kitchen, wooded views and total privacy- the perfect blend of upscale escape and outdoor adventure! Let this private space help you restore, recharge and reconnect.

Top Guest favourite
A rustic log cabin is surrounded by lush greenery, featuring a red metal roof and a large front deck. A stone pathway leads to the entrance, while multiple windows and a balcony are visible on the second floor, blending harmoniously with the natural landscape.
Cabin in Rindge
4.94 out of 5 average rating, 134 reviews

Lakefront 3BR Log Cabin w/ Dock & Fire Pit

Escape to our true log cabin on Lake Contoocook. Wake up to sparkling water views, step onto the private dock, and spend the day swimming, kayaking or fishing. Inside you’ll find soaring timber ceilings, a fully equipped kitchen, fast Wi-Fi and three comfy bedrooms that sleep eight. Lakefront deck for sunset drinks, fire pit & BBQ grill Board games & books for rainy days. Only 90 minutes from Boston yet a world away in the pines—perfect for families and friend getaways year-round.

Top Guest favourite
A modern home features a combination of dark siding and natural wood accents, positioned among tall trees. A welcoming porch extends from the entrance, complemented by an American flag. The surrounding area includes a gravel path and vibrant greenery, providing a serene atmosphere.
Home in Jaffrey
4.98 out of 5 average rating, 106 reviews

Willow Falls Home ~Hot tub & Waterfront

Constructed waterfall views are just feet away from you! Not far from Boston, RI or CT, this newly designed home is located at a privately viewed pond, in New England, near Mt. Monadnock! Kick back, relax & listen to the water falling in a screened-in gazebo, or in the outdoor hot tub! Or view it all at the picture windows and enjoy the solitude at this picturesque retreat! Inside you'll find multiple lounging areas, luxurious beds, a fully stocked kitchen and a fun game room.

Top Guest favourite
A single-story building with a dark exterior is surrounded by lush greenery and colorful flowers. The structure features multiple windows and a wooden front door. A gravel path leads up to the entrance, enhancing the inviting farmhouse setting.
Guest suite in Jaffrey
5.0 out of 5 average rating, 95 reviews

Relax with the View at the Farm at Woodbury Hill

Consider relaxing in our spacious upstairs apartment with a spectacular view of Mt. Monadnock. An open floor plan features a queen size bed and futon. A fully equipped kitchen will be stocked with 6 fresh farm eggs to enjoy as you like. Brew your own coffee or tea. All the needed linens and bathroom towels are supplied. Highspeed WiFi and Roku TV is available. You are welcome to walk the farm and enjoy the chickens or gardens. Or simply relax on your own private outside deck.

Top Guest favourite
A spacious dining area features a glass-top table surrounded by four chairs, illuminated by a modern light fixture. The vaulted ceiling with exposed wooden beams adds character. A beige sofa is positioned nearby, with large windows allowing natural light to fill the space.
Cottage in Harrisville
4.95 out of 5 average rating, 113 reviews

The Harrisville Ranch - Monadnock Region Getaway!

Located in the heart of the Monadnock Region and surrounded by forests and lakes the Harrisville Ranch is ready to host you! With 4 bedrooms it is great for groups & families visiting the area for hiking, weddings, or just a getaway to a quaint NH village. Mount Monadnock: 5-15 minutes depending on the hiking trail Dublin School: 5 minutes Aldworth Manor & Mayfield Farm Venues: 8 minutes Harrisville Center: 5 minutes Peterborough: 15 minutes Hancock: 15 minutes Keene: 20 minutes

Guest favourite
A vintage log cabin with a green metal roof is nestled among tall trees, showcasing a welcoming porch with seating. Vibrant blue adirondack chairs surround a fire pit, while a picnic table offers an inviting space for outdoor dining. The natural setting enhances the peaceful ambiance.
Cabin in Fitzwilliam
4.86 out of 5 average rating, 133 reviews

Charming Waterfront Log Cabin

Escape the daily grind at this unique & tranquil getaway. At the end of a quiet road, this vintage log cabin sits on a 150-acre pond to explore at your pleasure. Inside, the space features 2 bedrooms & a spacious loft. Listen to the sounds of nature by the fire pit, watch the sunset from the porch, or watch Netflix on our fiberoptic Wi-Fi. However you slice it, you'll leave The Pond Camp relaxed, rejuvenated, & ready to tackle whatever comes your way.

Guest favourite
A comfortable sofa is positioned near a window with sheer curtains, allowing natural light to illuminate the space. A decorative pillow with text is placed on the sofa, while a glass of wine rests on a wooden table outside, visible through the window.
Cabin in Winchendon
4.96 out of 5 average rating, 133 reviews

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

Top Guest favourite
Place to stay in Winchendon
4.93 out of 5 average rating, 103 reviews

Enjoy your stay in an Antique Home in a Toy Museum

Stay on the second floor of a 1780 Colonial House in a very unique toy museum. Winchendon is a quaint bedroom community known as "Toy Town". Located close to hiking trails, skiing, and lakes. The home is located right downtown, close to restaurants, bike trails and the library. You have access to a kitchen, 1 full bath, and 2 half baths. All rooms are well appointed, and period decorated.

Superhost
A wooden dock extends over the calm lake, featuring two Adirondack chairs positioned for lakeside relaxation. A vibrant rainbow arcs across a partly cloudy sky, while lush greenery frames the tranquil water, highlighting the natural beauty of the surroundings.
Cottage in Jaffrey
4.96 out of 5 average rating, 51 reviews

The Boathouse - A rustic and cozy lakeside cottage

Take it easy at this tranquil lakeside getaway. Enjoy over 100 feet of waterfront at the foothills of Mt. Monadnock. Rustic cottage on 1 acre of woods off a dirt road. 30’ of ‘L’ shape dock with 2 kayaks and 2 paddle boards. Outdoor fireplace, picnic table, and hammock trees provide for the ultimate in adventure and relaxation. Always hot and cold spring water, on demand!

Popular amenities for Jaffrey holiday rentals