Holiday houses in Cheshire County

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Cheshire County

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

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Guest favourite

Home in Antrim

4.98 out of 5 average rating, 168 reviews

Relaxing Hot Tub Getaway

Fully Stocked & Newly renovated 2 bed/1 bath with tons of appliances for cooking. Close by beaches, hiking trails & ski resorts. 1 mile from Gregg Lake Beach Professionally cleaned High speed WiFi ALL YEAR PRIVATE/SECLUDED HOT TUB Fire Pit, Grill, Hammock, Gym equipment Life Size Janga, Yahtzee, Darts, Corn Hole, Ping pong, mini pool table Electric Heating/cooling each room 2 KING PURPLE mattresses 2 sleeper couches 1 king air mattress 55' Amazon Fire TV in Living Room Vizio 55’ TV in Bedroom

Superhost

Tiny home in Town of Rockingham

4.78 out of 5 average rating, 92 reviews

Tiny Home w/ Parking - Pet Friendly & Fireplace!

Beautiful Bellows Falls Tiny Home named Sky’s the Limit! Anything is possible here. Please join us in the first ever unveiling of Airbnb for this quaint tiny home! It is near a plethora of shops and restaurants in the historic town of Bellows Falls. Explore for yourself, or bask in the heat of the fireplace inside the house and fire pit outside. For hikers and skiers, this home is a hidden gem. Okemo is just 37 minutes driving, and there are scenic running paths and hiking spots within town!

Guest favourite

Cottage in Antrim

4.98 out of 5 average rating, 62 reviews

Modern Quiet Lakeside Retreat

Come relax at our newly renovated lakefront home on Gregg Lake! Our spacious and modern home is located on a quiet cove of this 200 acre lake that boasts a variety of fun water activities. Enjoy the use of our kayaks, paddle boards and peddle boat or try your luck at catching some local bass with our fishing rods! You will also love the scenic sunsets you can view from our large deck that overlooks the lake. Tons of amenities included so that we can make your stay comfortable and stress free.

Guest favourite

Cabin in Stoddard

4.97 out of 5 average rating, 153 reviews

Stylish Waterside Retreat Surrounded by Nature

Mended Oar Outpost offers peace and solitude in a beautiful and secluded setting, part of the 250-acre Lakefalls Lodge estate. The view from the enclosed wraparound porch of Chandler Meadow and the adjoining 10,000 acres of conserved land is truly breathtaking. You can go swimming, hike for miles in the woods, or spend the day canoeing or kayaking from your private dock as you watch Chandler Meadow's otters, beavers and blue herons . You might even see a moose grazing at the water's edge.

Guest favourite

Cabin in Rindge

4.98 out of 5 average rating, 124 reviews

Lakeside Log Cabin near Mt Monadnock

Welcome to Cabin at the Cove! This spacious 4-bedroom 2-bathroom log cabin sleeps 10 + up to 2 dogs. The cabin offers rustic charm with modern amenities and is located just a 3-min drive to a community beach on Lake Contoocook! Vacation on a picturesque lake, hike to leaf peep from the top of beautiful Mount Monadnock, cross-country ski, or curl up with a book by the fire – there is something for everyone year-round. While only 90 minutes from Boston, it feels like a true nature escape.

Guest favourite

Apartment in Peterborough

4.94 out of 5 average rating, 70 reviews

Beautiful Home On The River

Book up to 6 people overlooking the beautiful Contoocook River in the heart of Peterborough! Within a 5 minute walk to Depot Square, this airbnb is bright, unique, with warm modern elements! Two bedrooms upstairs, the third bedroom in the porch which includes a queen bed. Conveniently walkable to Peterborough's restaurants, shops, and local events! Mount Monadnock only 18 minutes away, Pack Monadnock only 5 minutes away ~ Note: this is an entire apartment not just a single hotel room 🏡

Superhost

Home in Antrim

4.82 out of 5 average rating, 119 reviews

Quiet House in the Woods

Relax with the whole family at this peaceful place to stay. - Gregg Lake 5 mins away (Swim, Volleyball, Swings, Boat Docks) - Great hiking trails (Monadnock & Miller State Park) - Ski in the winter (Crotched Mountain 20 mins away, Pats Peak 30 mins away) - Small town: Mom & Pop shops/restaurants, Antique stores - 2 Decks: Out door dining & sitting areas This is not an investment property, this is my home. Please be respectful of the property. Thank you! Hope you enjoy your stay!

Guest favourite

Home in Spofford

4.75 out of 5 average rating, 40 reviews

Penthouse

Enjoy vacationing at the Penthouse. With magnificent views from the covered porch, overlooking the largest private beach on a premier clean NH lake with great fishing. The Penthouse is a charming remodeled house with wood cabin charm. This unit includes a 60" TV, high speed internet services, and a pellet stove for heating in the winter months. Just for fun: see if you can find some old love notes on the wood walls. We provide linens, towels, trash bags, and paper supplies.

Guest favourite

Home in Harrisville

4.9 out of 5 average rating, 10 reviews

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our cherished home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

Guest favourite

Home in Putney

4.89 out of 5 average rating, 102 reviews

Peaceful Beautiful Mountain Home Spectacular Views

15 Spectacular Acres! Plenty of room for the entire family or great for a couples getaway. This home has everything you need. There are brand new mattresses, quilts, linens, towels, cookware, plates and utensils for your comfort. The beautiful mountain views are seen from just about every room. There is a wood burning fireplace, 4 bedrooms and 2 full bathrooms. Both levels have 3 season porches to enjoy the views, coffee, reading or a meal.

Guest favourite

Home in Rindge

4.91 out of 5 average rating, 23 reviews

The Shoreline

Welcome to The Shoreline. This Classic New England Lakehouse is located on Lake Monomonac, minutes away from amenities but tucked away in small town America. This property is the ideal getaway for a relaxing vacation. The kitchen and living areas are comfortable and clean, but the real star is the lake itself—perfect for boating, kayaking, swimming, and fishing. Enjoy the 180 degree water views and over 500 ft of beautiful shoreline.

Guest favourite

Guesthouse in Putney

4.97 out of 5 average rating, 279 reviews

Cozy cottage loft and retreat

Relax and recharge in our peaceful Vermont cottage. Enjoy this sweet getaway with hardwood floors, fast wifi, a fully equipped kitchen, a quiet sleeping loft with a queen size bed, gorgeous natural light, views of surrounding hills and pond, gardens, and your own private entrance and back deck next to the Putney Brook.