Vacation rentals in Cheshire County

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Top-rated vacation rentals in Cheshire County

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Top guest favorite

A covered wooden bridge with a red roof is seen next to a calm waterway, surrounded by trees displaying autumn foliage. A wooden dock extends into the water, enhancing the tranquil setting. The landscape reflects a natural, serene environment.

Cabin in Stoddard

4.98 out of 5 average rating, 160 reviews

Secluded Renovated Retreat Surrounded by Nature

Get away from it all in a secluded, yet modern cabin, which guests have loved for its "silence and beauty" and called "peaceful" and "serene". Located on the Lakefalls Estate, which maintains the roads, Mended Oar features heated floors throughout, a well-furnished kitchen with quality appliances and equipment, and luxurious linens. Hike the many trails outside the door on the snowshoes you'll find, then come inside to enjoy the wood burning fireplace (wood provided) and play a board game.

Top guest favorite

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 favorite

A billiards room features a vibrant red pool table at its center, surrounded by wooden flooring. Natural light floods in through large windows, highlighting the contemporary decor. An antler chandelier hangs above, while colorful glass items are displayed on a sleek, white shelf against the wall.

Home in Bellows falls

5 out of 5 average rating, 9 reviews

Amazing Views, Skiing Nearby and Amenities Galore!

Discover your perfect getaway at our stunning rental, nestled in the heart of Rockingham. Boasting breathtaking views, this home is an ideal retreat for ski enthusiasts and those seeking a tranquil escape. With 5 large bedrooms and 3 modern bathrooms, it comfortably accommodates your family or group. Enjoy the convenience of a fully equipped kitchen, billiards room, sauna and much more. Experience the ultimate vacation, close to skiing adventures and all the amenities you could wish for.

Superhost

A serene lake is depicted, with calm waters reflecting the blue sky and scattered clouds. The shoreline is lined with lush greenery and smooth stones, creating a natural border. Distant trees are visible, framing the peaceful scene.

Home in Antrim

4.8 out of 5 average rating, 126 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 favorite

A wooden deck provides a serene view of Highland Lake, framed by colorful autumn foliage. Tall trees surround the area, reflecting the natural beauty of the season. The cabin's sloped roof enhances the rustic charm, creating a peaceful outdoor space.

Cabin in Washington

4.94 out of 5 average rating, 106 reviews

Beautiful Log Cabin on Highland Lake

Take it easy at this unique and tranquil getaway. A gorgeous log cabin nestled right on Highland Lake in Washington, NH. An outdoor lovers paradise that welcomes you any season. Nearby Mount Sunapee, Mount Manodnock, Crotched Mountain, Pillsbury State Park and Pats Peak. fall foliage, fire pit, grilling, ATV trails ice fishing, nearby skiing, snowmobile trails boating, kayaking, swimming, fishing Get the full New England experience at this incredible lakeside location!

Guest favorite

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 favorite

A serene outdoor space is highlighted by a grassy area beneath tall trees. A clear view of the calm lake is visible in the background, with a swing set and picnic tables nearby, fostering a relaxing environment for guests.

Home in Antrim

4.98 out of 5 average rating, 181 reviews

Relaxing Hot Tub Getaway

The ultimate experience for couples & families 5-10min from hiking trails & ski resorts A Mile from Gregg Lake Beach ALL YEAR PRIVATE/SECLUDED HOT TUB Grill, Hammock, Gym equipment XBox Series S, Life Size Janga, Yahtzee, Darts, Corn Hole, ping pong table, mini pool table Luxury KING PURPLE Brand Mattresses in every bedroom for the best nights rest with individual mini splits for optimal comfort Fully stocked kitchen High speed WiFi, house on 2 private acres

Top guest favorite

A fire pit surrounded by six chairs is set on a stone patio, offering a cozy gathering space. A sandy beach leads to a private dock with kayaks and paddleboards visible on the water. Lush greenery and a clear lake view create a serene outdoor environment.

Cottage in Winchendon

4.98 out of 5 average rating, 42 reviews

Top 10 of VRBO -Copley's Lakefront Cottage on Lake

A very unique, beautifully designed Belgium Farm House on Lake Monomonac, who's waters straddle both Massachusetts and New Hampshire. Your own sandy beach and dock to enjoy everything the lake has to offer. All seasons can be thoroughly enjoyed here; boating, fishing, swimming and other water sports in the summer, vibrant colors and crisp air of fall, in the winter enjoy iceskating and fishing, then end the day with a good book by the fireplace.

Guest favorite

The exterior of a two-story wooden home is shown, surrounded by a lush green lawn. A large tree provides shade, while the blue sky features scattered clouds. A relaxed seating area is visible on the grass, enhancing the scenic countryside setting.

Home in Putney

4.89 out of 5 average rating, 103 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 favorite

Home in Rindge

4.94 out of 5 average rating, 31 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.

Top guest favorite

A charming red cottage is nestled among lush greenery and colorful blooming flowers. Sunlight bathes the exterior, highlighting the welcoming double doors and large windows that offer views of the natural surroundings.

Guesthouse in Putney

4.98 out of 5 average rating, 314 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.

Superhost

A rustic cabin with red shingle siding features a welcoming porch with a wooden railing. A seating area is visible on the deck, complemented by a dark grill. Large windows allow natural light to illuminate the inviting entrance.

Cabin in Hillsboro

4.86 out of 5 average rating, 44 reviews

Cabin in the Woods

Rustic-Yet-Modern Fully Renovated 3 bedroom New Hampshire hideaway located on a tree lined dirt road in a 1.5 acre wooded landscape. Unwind in style while enjoying local: ~ Skiing ~ Lakes ~ Fishing ~ Hiking ~ Golf ~ Restaurants ~ Picturesque Foliage ~ Family-Friendly & Cozy with all of the Comforts of Home ~