
Pet-friendly holiday 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.

Peaceful Mountain Cottage Above Private Meadow
Great for skiers and writers alike. Nestled within a mountaintop meadow, through a covered bridge & above a small Vermont village, our peaceful cottage is a destination and provides brilliant fall foliage and Vermont's natural beauty. We feel the oxygen and restorative negative ions here on the land from the lush mountain woods; true shinrin-yoku ('forest bathing'). Skiing, hiking, biking, gourmet restaurants, live music, cafés, coffee shops, & health/international market & co-ops exist nearby.

Cozy Cabin with Lake Access
Our cabin is situated in a private, peaceful setting surrounded by trees. Inside you will find a timeless lake house decor and everything you need for a relaxing vacation. A 1/4 mile walk or drive brings you to our private community lake access and boat ramp on beautiful Highland Lake. We offer use of our 3 kayaks (2 single/1 tandem) located next to the boat ramp. Nearby are great hiking trails and quaint villages. This is a wonderful place to unwind and have a truly fun & relaxing vacation!

Direct Waterfront A-Frame, Close to 3 Ski Areas!
My direct waterfront, year-round A-Frame cabin is 30 min to Mount Sunapee, 20 min to Crotched, and 15 min to Pat's Peak! It’s located on a small 32-acre pond near Franklin Pierce Lake with over 100 feet of waterfront. There is a 6 foot main dock to load kayaks, and a small fishing dock off to the side. The fishing on our pond gets rave reviews! The property sits on 1/3 of an acre, on a sloped hill. It's located between Keene and Concord, and nearby many great hiking and snowmobile trails

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.

The Harrisville Ranch - Monadnock Region Getaway!
Located in the heart of the Monadnock Region and surrounded by forests and lakes the Harrisville Ranch is ready to host you! With 4 bedrooms it is great for groups & families visiting the area for hiking, weddings, or just a getaway to a quaint NH village. Mount Monadnock: 5-15 minutes depending on the hiking trail Dublin School: 5 minutes Aldworth Manor & Mayfield Farm Venues: 8 minutes Harrisville Center: 5 minutes Peterborough: 15 minutes Hancock: 15 minutes Keene: 20 minutes

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!

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.
Popular amenities for Cheshire County pet-friendly home rentals
Pet-friendly house rentals

Beautiful post and beam home by waterfall.

Spacious Brattleboro home on river, walk to town

Island Pond Cottage, pet friendly, walk to deli

Amazing Views, Skiing Nearby and Amenities Galore!

Charming, Large House in Walpole NH /VT. Border

Country Cottage

The River House

Harrisville Lake House - A Tranquil Get-Away
Pet-friendly home rentals with a pool

Moose Mansion with Paw Pen at Brattleboro KOA

The Shoreline

The Brick House on Washington Street

Rocky Ledge: Cozy Pet-Friendly 3BR Log Cabin

Log Cabin at Brattleboro KOA
Private, pet-friendly home rentals

Lakefront family vacation home

Magic Lakehouse, Waterfront, Private Beach & Dock

Cobb Meadow House - Cozy 5 Bedroom New England hom

Serenity - Fantastic Spacious House In Quaint VT

Recharge in a yurt at REST Farm Campground

Bright 2BR Escape with Office Near Downtown Keene

Beautiful Victorian Home

GiGi's Cabin/ 314' Shoreline
Destinations to explore
- Rentals with a patio Cheshire County
- Apartment rentals Cheshire County
- Farmstay rentals Cheshire County
- Rentals with breakfast Cheshire County
- Rentals with lake access Cheshire County
- Rentals with a washing machine and dryer Cheshire County
- Guesthouse rentals Cheshire County
- Rentals with a fire pit Cheshire County
- Rentals with a kayak Cheshire County
- Family-friendly rentals Cheshire County
- Beachfront rentals Cheshire County
- Rentals with a hot tub Cheshire County
- House rentals Cheshire County
- Rentals with outdoor seating Cheshire County
- Rentals with pools Cheshire County
- Private suite rentals Cheshire County
- Rentals with a fireplace Cheshire County
- Tiny house rentals Cheshire County
- Waterfront rentals Cheshire County
- Pet-friendly rentals New Hampshire
- Pet-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Stratton Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Snhu Arena
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Bear Brook State Park
- Bromley Mountain Ski Resort
- Mount Sunapee Resort
- Emerald Lake State Park
- Smith College
- University of Massachusetts Amherst
- Crotched Mountain Ski and Ride
- Mount Holyoke College
- Mount Monadnock
- The Montague Bookmill
- Southern Vermont Arts Center
- Camp Plymouth State Park





