
Pet-friendly vacation rentals in Cheshire County
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Cheshire County
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Boulder House - Extraordinary Luxury in the Woods!
From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Chalet Sonsie: A Sweetwater Stay
Chalet Sonsie is a freshly-renovated waterfront getaway, where you can enjoy breathtaking views of Forest Lake year-round, from every room and all 3 levels of decks! Whether you're traveling with the kids, friends, or just looking for a quiet fishing retreat, there's something here for everyone. This cozy 2-bedroom home features 2 full kitchens, 1.5 baths, expansive fireplace and TV, plus a game room complete with foosball and mini-arcade! Book today, or check out other Sweetwater Stays! -Patti

Private Apartment with a Mt. view
*We may make special exceptions for a dog. $50.00 fee per night. *The water from our well is excellent Comfortable, private apartment in a Mid-Century Modern house with stunning views of Mt. Monadnock and farm. 1 Bedroom with Queen Bed w/AC sleeps 2. NOTE: $50 fee for each bed after main bed. Fully equipped Kitchenette, Huge bathroom & Living room -Queen Hide-a-bed sleeps 2. NOTE: We have internet TV, but no cable. So please remember to bring your sign in information for Netflix and Amazon.

Rocky Ledge at Highland Lake: Cozy 3BR Log Cabin
Nestled within the woods of Stoddard, NH, Rocky Ledge is a peaceful year-round family retreat. Our cozy log cabin has 3 bedrooms, 2 bathrooms, and a lower-level den perfect for family time. Enjoy outdoor dining on the large 3-sided deck, and cap off your days with s'mores sessions at the fire pit! Boating, hiking, swimming, and skiing are minutes away. Or, get cozy indoors and enjoy movies, puzzles, and games. Rocky Ledge is pet-friendly! We welcome up to two dogs with a flat $50 pet fee.

The Brick House on Washington Street
Three guest bedrooms in a Colonial home on Washington Street make a great launchpad for visitors to Keene. From here, it's a pleasant walk or drive to Downtown restaurants, the theatre and shops. The Sterling family has owned this pretty place since 1982 and a design studio operates in the barn portion of the space. The open living room with TV and original fireplace adjoin a "tea room" with a bright bay window. Family chef-approved, guests are welcome to use the spacious kitchen.

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!

The Great Room in Historic Fitzwilliam
Come relax in the great room! Large space with full bathroom, beautiful picture windows, spacious closet, and use of deck included. Deck includes a cozy fire pit table, gas grill, and a nice view of the beaver pond, great for bird watching! Please don't hesitate to reach out if you are traveling with children and/or pets, we are often able to accommodate on a case by case basis. Please note stairs are required for entry via the deck entrance.

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.

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.

Cabin getaway in Southern Vermont
Let us share our little piece of Vermont with you! Located off a dirt road, tucked into a corner of our working homestead, you'll find a space to relax, unwind, and reconnect. This cabin has everything you need for a private and comfortable escape. Downstairs you’ll find a comfortable leather couch, small kitchen, & bathroom with vanity & shower. The bedroom (located upstairs) has a queen sized bed. All linens provided.

Vermont Retreat Cabin, Romantic, Nature Immersion
A romantic and private getaway on a peaceful six-acre farm with views of fields and forest. ☽ Featured in STAY; Gorgeous Cabins of the East Coast ☽ Elevated design; thoughtful lighting; deeply romantic ☽ Quiet & private; star-studded skies ☽ Woodstove, deck, reading nook, firepit ☽ Local's Area Guide with our favorite spots ☽ Strong wifi, no TV ☽ Scrupulously clean using unscented products

Apartment on Main Street
One bedroom apartment with kitchenette (mini-fridge, coffee maker, microwave, dishes etc.), full bathroom with laundry, and open living space. I am an English teacher, so there are lots of books! Apartment is located in the Village of Saxtons River- within easy walking distance from the Market, Vermont Academy, our new Park, and Main Street Arts.
Popular amenities for Cheshire County pet-friendly home rentals
Pet-friendly house rentals

Little House with Lots to Offer

Cobb Meadow House - Cozy 5 Bedroom New England hom

Spacious Brattleboro home on river, walk to town

Amazing Views, Skiing Nearby and Amenities Galore!

Charming, Large House in Walpole NH /VT. Border

Country Cottage

Harrisville Lake House - A Tranquil Get-Away

Modern Cottage / Farmhouse
Private, pet-friendly home rentals

Lakefront family vacation home

Magic Lakehouse, Waterfront, Private Beach & Dock

Serenity - Fantastic Spacious House In Quaint VT

Recharge in a yurt at REST Farm Campground

Best Summer Lakeside Cabin in NH - The Jaffrey Gem

Lake Front Campsite 🏕

The Harrisville Ranch - Monadnock Region Getaway!

Honeymoon Cottage at the Lake
Pet-friendly home rentals with a hot tub

Direct Waterfront A-Frame, Close to 3 Ski Areas!

83-Acre Getaway: Hot Tub, Pool Table, NatureTrails

Great Meadow Main House: Putney, Vermont

Spacious Loft with View

Vermont Retreat Luxe Yurt, Romantic & in Nature

Private Teepee “Glamping”

Maple Hollow Mountain Hideaway with Hot Tub
Destinations to explore
- Rentals with breakfast Cheshire County
- Tiny house rentals Cheshire County
- Waterfront rentals Cheshire County
- Rentals with lake access Cheshire County
- Guesthouse rentals Cheshire County
- Private suite rentals Cheshire County
- Rentals with a patio Cheshire County
- Rentals with a fireplace Cheshire County
- Farmstay rentals Cheshire County
- Rentals with a washer and dryer Cheshire County
- Beachfront rentals Cheshire County
- Cabin rentals Cheshire County
- Rentals with outdoor seating Cheshire County
- Family-friendly rentals Cheshire County
- Rentals with a kayak Cheshire County
- Rentals with a fire pit Cheshire County
- Apartment rentals Cheshire County
- Rentals with a hot tub Cheshire County
- Pet-friendly rentals New Hampshire
- Pet-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Monadnock State Park
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Bear Brook State Park
- Mount Snow Ski Resort
- Manchester Country Club - NH
- Nashoba Valley Winery, Distillery, Brewery and Restaurant
- Nashoba Valley Ski Are
- Ragged Mountain Resort
- Mount Sugarloaf State Reservation
- Nashua Country Club
- Derryfield Country Club
- Mount Tom State Reservation
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Dorset Field Club
- Hooper Golf Course
- Whaleback Mountain
- The Shattuck Golf Club




