
Pet-friendly holiday rentals in Cheshire County
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Top-rated pet-friendly home rentals in Cheshire County
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Pet-friendly house rentals

Secluded lakefront vacation home
Beautiful home. Well kept. Hosts super accessible and very friendly. We felt like home and house is super cozy

Magic Lakehouse, Waterfront, Private Beach & Dock
Our stay at the Magic Lake house was wonderful. There is plenty of room, it is very well stocked with games, books, toys, and yard games, and the lake was beautiful to kayak. We enjoyed cooking out, sitting by the fire pit in the evenings, and hanging out on the deck. Such a great place to visit with family. Hannah and Dave were very timely in sending information and answering any questions we had. We would definitely stay there again!

Little House with Lots to Offer
Julie was a great host. The house is tucked away so it’s a bit hard to find but her directions helped us find it easily. The yard was great for the dogs and the dogs loved the beds and dog toys. The house was clean and had everything we needed. We were very happy to be able to stay in a dog friendly place so we could see family for Easter. Thank you!

Serenity - Fantastic Spacious House In Quaint VT
The space is great for larger parties to sit together and enjoy dinner or hanging out. In the center of town yet quiet and felt like home away from home. The fireplace and access to firewood was great. Chris was friendly to communicate with and responded quickly. We were all very happy with our stay

Hazelhurst Vacation House
You walk into Eric’s place and it feels like a home thoughtfully set up so that you can just walk in and be comfortable. It’s an “and, breathe” kind of relaxing, homey place. Eric was super responsive to any & all questions we had. We absolutely loved our time there and look forward to rebooking in the future!

The Brick House on Washington Street
We had a great stay in Keene. Ruth is a fantastic hostess. Her house is just close enough to Main Street to keep it a walkable distance to multiple restaurants and shopping. The house is a nice cozy spot that was big to accommodate my whole family meeting up for a fun winter weekend in Keene. I would stay there again without hesitation

Charming, Large House in Walpole NH /VT. Border
Karen's place was just what we were hoping for, a cozy historic home with plenty of space to spread out and relax after a long drive. Absolutely would stay here again. The details: well stocked kitchen, hot showers with good water pressure, comfy beds, cosy furniture, quiet amd peaceful stay.

The River House
We had a lovely time at this place, it’s a bit small but we’ll appointed and you can’t beat the location, right on the river! The views out the back were incredible every day. This didn’t impact us but be aware the upstairs loft area is probably better for children and a tall adult would feel pretty cramped up there. As a rather short crew my family had no problems 😂. Would definitely stay again.
Private, pet-friendly home rentals

Beautiful Victorian Home
Barbara, was an amazing host. Her house is absolutley beautiful. Amazing kitchen, that is perfect, for so many occasions. Very kid frinedly, our family loved staying here, would highly reccomend. Quick to reapond and gives tips and reminders or important information as to where things are 😊

Storybook Lake Front Villa with Private Beach!
House was very clean and had such a beautiful view of the Lake.

Heron Cove Cottage: A Sweetwater Stay
Was a very nice peaceful place for a few weeks

Waterfront Coopers' Barn
Lovely space and surroundings! Peaceful retreat! Kind, helpful and responsive hosts! Easy to stay comfortably, amenities well considered, clean and tidy space. Front door lock was a little fritzy, but armed with host's tips it always worked in a minute or two. Back deck was AWESOME. Cool old school pin ball machine in the living room and in good working order! Be prepared to be asked to remove all trash / recycling at the conclusion of your stay. Absolute pleasure, would definitely consider returning!! Thanks Rob and Patty!

Simple 2+ bed, no frills, all necessities covered!
Great place, especially for the budget. It was clean, comfortable, and had everything we needed for a relaxing stay.

Camp Site on Private Pond with Lake access
Raymond wss a great host. He was very responsive and helpful! The A Frame is lovely and the campsite is well stocked with thoughtful necessities. It was a really peaceful weekend away!

Water views, 2 min to public beach, 4 bedrooms
I had an excellent experience staying at Jennifer’s place! The home was exactly as described—clean, comfortable, and well-stocked with everything I needed. The location was perfect for enjoying a quiet weekend. Jennifer was a wonderful host very attentive and respectful.

House on a hill
Very close to Keene and Vermont. Great area overall. The house was a great size for two people and a dog. Very clean and welcoming. Thank you for a great stay!
Pet-friendly home rentals with a hot tub

Direct Waterfront A-Frame, Close to 3 Ski Areas!
What an absolutely wonderful experience! Emily was beyond caring and friendly, and I truly enjoyed every minute at this cabin. The water is beautiful, and the cabin was always cozy. I especially loved the beautiful kitchen, it was a dream! I highly recommend anyone to visit, definitely worth it!

Boulder House - Extraordinary Luxury in the Woods!
The best airbnb ever, me and my wife enjoyed a lot, local is really private, everything was pretty clean, kitchen was complete with all basic utensils, at main lodge the guy borrowed his golf cart. Everything was perfect, it was worth. I will be back of course! Thanks Don!

Charming Lake Front Home
A great spot for R & R! We loved being right in the lake, great view, private and quiet, hiking, walking trails, kayaking! Plenty of room to spread out! Clean and all amenities supplied! We enjoyed family and friends through the week. Local to Mt Madanock.

Private Teepee “Glamping”
My boyfriend and i had a great one night get away! Even though it rain majorly of the time we were there, it was a really nice location. Loved the wood fire hot tub. Boathouse stayed toasty warm through the night. And my dogs loved the pond and running and playing! Definitely want to return with our kids for a weekend stay and hopefully a dryer one, i wanted to stay in the tipi! Definitely recommend to anyone who wants an off grid experience!

Cabin getaway in Southern Vermont
Such a cozy place to stay! It has that homestead feel for sure that we loved. Nick is a really chill and gracious host. When the hot tub was having an issue he quickly came to check it out and troubleshoot and immediately offered to let us use the other rental on the property’s hot tub, which was so cool because the view from that hot tub was awesome. I definitely want to come back here soon!
Destinations to explore
- Rentals with a firepit Cheshire County
- Beachfront rentals Cheshire County
- Rentals with a kayak Cheshire County
- Rentals with breakfast Cheshire County
- Family-friendly rentals Cheshire County
- Rentals with a washing machine and dryer Cheshire County
- Rentals with outdoor seating Cheshire County
- House rentals Cheshire County
- Rentals with a patio Cheshire County
- Rentals with a fireplace Cheshire County
- Farm stay rentals Cheshire County
- Rentals with lake access Cheshire County
- Flat rentals Cheshire County
- Rentals with pools Cheshire County
- Rentals with a hot tub Cheshire County
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- Stratton Mountain
- Okemo Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Pats Peak Ski Area
- Ragged Mountain Resort
- Berkshire East Mountain Resort
- Mount Snow Ski Resort
- Aaronap Cellars
- Mount Sugarloaf State Reservation
- Manchester Country Club - NH
- Nashoba Valley Ski Are
- Bear Brook State Park
- Ekwanok Country Club
- The Shattuck Golf Club
- Hooper Golf Course
- Nashua Country Club
- Baker Hill Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Clarksburg State Park
- Stump Sprouts Ski Touring Center