Vacation rentals in Jaffrey

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Top-rated vacation rentals in Jaffrey

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Top guest favorite
A serene pond reflects the white cottage and surrounding trees, creating a tranquil scene. Wildflowers and grasses frame the water's edge, while lush greenery enhances the natural beauty of the area. The peaceful environment is ideal for relaxation and outdoor exploration.
Cottage in Petersham
4.99 out of 5 average rating, 222 reviews

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Top guest favorite
Apartment in Dublin
4.97 out of 5 average rating, 255 reviews

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.

Top guest favorite
The exterior of The Ginger Bed is showcased, featuring a light green facade with white trim around the windows and door. A welcoming orange door is prominently displayed, surrounded by a landscaped area with colorful mums and autumn foliage.
Guest suite in Ashburnham
4.98 out of 5 average rating, 490 reviews

The Ginger Bed King Suite

Come for the lovely country setting, the winter beauty, amenities, neighborhood, convenience, privacy, spaciousness, and the comfortable bed. Close to many wonderful hiking/biking paths, rail trails, Wachusett ski area, Jewel Hill, Lake Wampanoag, Kirby area. WI-FI, TV ( Hulu and Netflix), refrigerator, microwave, coffee/tea maker, reading lights, table area, continental breakfast, parking... Good for couples, solo and business travelers. (Key pad for Covid safe entry) Everyone is welcome!

Guest favorite
Guesthouse in New Ipswich
4.95 out of 5 average rating, 388 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)

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
4.88 out of 5 average rating, 113 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 with access to kayaks 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, paddle on the pond, 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 favorite
Guest suite in Fitzwilliam
4.95 out of 5 average rating, 358 reviews

The Carriage House in Historic Fitzwilliam

Welcome to the Carriage House! Former site of the popular Hannah Davis House Bed and Breakfast, this gorgeous space is ready for your visit! Beautiful wood beams throughout, a cozy loft bedroom, and a completely separate entrance for privacy. Short rides to Rhododendron State Park, Mount Monadnock, Gap Mountain, the Cheshire Rail Trail, Laurel Lake, and many more outdoor activities year round. Walking distance to the town common in a town where little has changed and history is preserved.

Guest favorite
A cascading waterfall flows over natural rocks, surrounded by lush greenery. Delicate pink flowers in the foreground enhance the serene setting, where the sound of rushing water and natural beauty create a peaceful atmosphere.
Guesthouse in Wilton
4.94 out of 5 average rating, 665 reviews

Cottage beside a waterfall

Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

Top guest favorite
A charming wooden cottage is surrounded by trees, featuring a screened-in porch. The exterior showcases warm, natural tones with a combination of shingles and wood paneling. A gravel path leads to the entrance, bordered by vibrant flower beds.
Cabin in Harrisville
4.96 out of 5 average rating, 205 reviews

Trailside Cottage in charming Harrisville, NH

Hike, bike, cross-country, snowshoe, or just inhale/exhale and enjoy the peace and quiet of a classic New England escape. Welcome to Trailside Cottage, a charming getaway in Harrisville, NH. Recently converted into a cozy space for two. It sits alongside one of the many trails in the Harrisville area, and is accessible to all of the amenities in the Monadnock Region. Our small farm is next door which means you might hear the sounds of country life including our donkey who brays at times!

Guest favorite
A vintage school bus is parked on a grassy area near a rustic barn. The bus features large windows and a worn white exterior, with an adjacent chair placed in front. Surrounding elements include patches of grass and scattered branches, contributing to the rural setting.
Tiny home in Jaffrey
4.88 out of 5 average rating, 112 reviews

Vintage School Bus by Monadnock

Stay in a vintage School Bus tiny home tucked behind a rustic 19th century barn at the base of a picturesque grass covered hill! Practically in the shadow of Mount Monadnock, the country's most hiked mountain is just a ten minute drive away! Full amenities include running water, a hot outdoor shower, and a porta potty restroom that's professionally cleaned every week! Vintage decor and antique furniture from our very own antique shop make your bus-away-from-home a cozy and charming getaway!

Guest favorite
An inviting open living space showcases warm brick walls and original timber beams. A spacious seating area features a brown leather couch and wooden coffee table, while a grand piano occupies one corner. Large windows with serene views of the outdoors offer natural light.
Loft in Peterborough
5 out of 5 average rating, 208 reviews

Peaceful Mill on the Water - Home Away from Home

Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated workspace.

Top guest favorite
A warm kitchen area features wooden paneling and a round dining table set for two. A small, cozy electric stove is situated near the table. The space is complemented by a full-size refrigerator and a microwave, with decorative touches on the walls.
Apartment in New Ipswich
4.95 out of 5 average rating, 114 reviews

Quiet country apartment in farmland setting.

Cozy studio located on 90 acres of private property that includes conservation woodland and fields, perfect for a challenging hike and wildlife viewing. Apartment has 1 queen bed with roll out cot and a full bathroom with shower and selection of towels. The fully equipped kitchen comes with a refrigerator, microwave, and the washer and dryer downstairs mean less packing. When not out and about exploring the countryside there is WiFi and a smart TV to keep you entertained.

Guest favorite
The open-concept kitchen and living area features natural wood paneling and high ceilings with exposed beams. A spacious kitchen island, accompanied by three wooden stools, provides ample counter space. Large windows allow natural light to illuminate the inviting space, while shelves filled with books line the walls.
Apartment in Nelson
4.89 out of 5 average rating, 105 reviews

Swiss Chalet Family Retreat!

Welcome to our family's Swiss style chalet! Inspired by trips to Davos, Switzerland, my grandparents built the chalet in the 1950s to be a family playhouse and gathering spot for their 6 children. It's kind of magical. Today, our large extended family still enjoys holiday celebrations here every year. Our kids love exploring the woodland trails and swimming in Center Pond. We hope you love it as much as we do! Note: the building also has two apartments on the first floor.

Popular amenities for Jaffrey vacation rentals

When is the best time to visit Jaffrey?

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Avg. priceG$29,249 GYDG$33,846 GYDG$34,472 GYDG$32,592 GYDG$31,130 GYDG$33,010 GYDG$35,308 GYDG$34,472 GYDG$33,637 GYDG$30,294 GYDG$27,996 GYDG$31,339 GYD
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Frequently Asked Questions

  • Do house rentals in Jaffrey have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Jaffrey. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Jaffrey?

    Jaffrey has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Jaffrey have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Jaffrey. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Jaffrey?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • How much does it cost to stay in house rentals in Jaffrey?

    Experience the best of Jaffrey with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Jaffrey have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Jaffrey. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Jaffrey?

    Yes! Work meets play with ease at over 10 vacation rentals in Jaffrey featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Jaffrey have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Jaffrey. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Jaffrey

  • Total vacation rentals

    Explore 30 vacation rentals in Jaffrey

  • Nightly prices starting at

    Jaffrey vacation rentals start at G$14,625 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,550 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Jaffrey vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Jaffrey rentals

  • 4.9 Average rating

    Jaffrey stays are highly rated by guests—averaging 4.9 out of 5!

  1. Airbnb
  2. United States
  3. New Hampshire
  4. Cheshire County
  5. Jaffrey