Vacation rentals in Jaffrey

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Top-rated vacation rentals in Jaffrey

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Top guest favorite

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

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.

4.91 out of 5 average rating, 118 reviews

Top guest favorite

A lush garden landscape is presented, featuring blooming pink azaleas alongside vibrant greenery. A tranquil stream runs through the garden, flanked by an array of flowers and well-maintained grass, surrounded by dense trees, creating a serene natural environment.

Apartment in Dublin

Private Dublin apartment nestled in the woods

Nestled in the quiet woods just north of Mt. Monadnock our cozy one bedroom apartment invites the outdoors in with peeks of the mountain through the trees. Sit out on your private deck and enjoy the view or stroll around the yard and pick a few blueberries in season. We welcome hikers, nature lovers, those visiting friends or family or just wanting to enjoy the area's beautiful scenery and many artistic venues. I like to think of it as a peaceful sanctuary that we'd like to share with you.

4.97 out of 5 average rating, 290 reviews

Top guest favorite

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

"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)

4.95 out of 5 average rating, 433 reviews

Top guest favorite

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

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.

4.94 out of 5 average rating, 135 reviews

Top guest favorite

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

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.

4.98 out of 5 average rating, 108 reviews

Top guest favorite

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

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.

5.0 out of 5 average rating, 97 reviews

Top guest favorite

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

Tranquil Pond Retreat | Mins to Mt. Monadnock

Escape to 8+ private acres in beautiful Jaffrey, New Hampshire. This spacious 3BR/3BA lodge features a tranquil private pond, two peaceful decks, two living areas, a chef’s kitchen, and wooded views in every direction. Just 10 minutes from Mount Monadnock, you’re perfectly positioned for hiking, exploring, and year-round adventure. Spend your days outdoors, then come home to total privacy and room to relax, reconnect, and recharge in your own New England retreat.

4.89 out of 5 average rating, 109 reviews

Top guest favorite

A serene view of a river bordered by lush greenery and colorful autumn foliage. The water reflects vibrant hues of blue and gold, creating a peaceful atmosphere. A wooden railing lines the bank, adorned with seasonal flowers, enhancing the natural beauty of the setting.

Loft in Peterborough

1850 Waterfall Mill-Loft Style Chic

IMMACULATE COUNTRY HOME W/ FAST WiFi in fresh air New Hampshire. Snuggled in on a quiet street, yet steps away from DOWNTOWN, two "Mini Whole Food" markets! State-of-the-art gourmet kitchen fleshed out with organic spices, wares for entertaining, and other luxuries such as a rReverse Osmosis drinking faucet. Stunning sunlit water views and soothing water sounds! Beautiful antique furnishings and marble finishes add to the unique beauty of this New England home.

4.96 out of 5 average rating, 316 reviews

Guest favorite

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

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.

4.86 out of 5 average rating, 133 reviews

Guest favorite

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

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.

4.96 out of 5 average rating, 137 reviews

Guest favorite

A bright living space features a comfortable sofa, a modern electric fireplace, and a television mounted on the wall. Natural light filters through the room, complemented by houseplants and a decorative bowl on a wooden coffee table. The open layout connects to an adjoining area.

Apartment in Peterborough

Cute, Quiet, Art-Filled Apt.

This above-garage apartment is cozy and comfortable. Perfect getaway! Just 1.5 miles from Peterborough in the beautiful Monadnock region this gem has easy access to trails (backyard) and lakes. Quality linens, tasteful decor, great coffee and a spot to stash all your gear in the breezeway. Guests share main entrance with owners (but separate dwelling) who respect your privacy. Apartment access thru narrow stairs off breezeway.

4.92 out of 5 average rating, 133 reviews

Guest favorite

Place to stay in Winchendon

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.

4.9 out of 5 average rating, 105 reviews