
Holiday rentals in Hillsborough County
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Top-rated holiday rentals in Hillsborough County
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Elegant Lodging in the Woods ~Privacy & Comfort!
Looking for a relaxing escape? As Superhosts with 6 years of 5-star reviews, we warmly welcome you to our smoke-free, private guest suite. Perfect for couples or solo travelers seeking comfort & tranquility. Tucked away in the peaceful countryside near Pat's Peak & Crotched Mountain, our location offers convenient access to skiing, hiking, golfing, scenic lakes, and the charm of rural New England. Enjoy the comfort of serene surroundings & experience genuine hospitality. 75 minutes from Boston.

"The Porch" Your cozy home away from home!
Welcome to The Porch! Ready for a mini vacation, or just a place to hang out, or work from? You are most welcome here! . This cozy cabin is very flexible and user friendly! It is private to only your group! The downstairs with all it offers, is for one or two person stays. The upstairs becomes available if you enter 3 or more people. This building is in the backyard of our home, as in photos on our Airbnb site, Other info is listed there also! Info book is in room! Welcome! (no pets)

Cottage beside a waterfall
Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

Guest suite with king bed and private entrance
Come and relax in our spacious one-bedroom basement guest suite that is comfortable and bright. It has a private entrance with off street parking. The suite has a large living area, bedroom with king bed and private bath . The location is an ideal 20 minutes from the Manchester/Boston Regional airport and 10 minutes from the Merrimack Premium Outlets as well as a wide variety of restaurants. Boston, skiing, the beach and the #1 most hiked mountain in the world are all about an hour away.

New England Village Luxury Studio
Kick back and relax in this stylish studio! Our house is in a quiet neighborhood of older homes surrounded by woodlands yet conveniently located downtown, a half mile from our village green (Milford Oval). A short stroll over the river will take you to cafes, restaurants, pubs with live music, post office, library, shops & useful stores such as CVS. Whatever brings you…business, skiing, hiking, antiques, a family celebration or a romantic weekend away…we are looking forward to hosting you!

Bear Brook Trail Side Getaway & RV Park
Come stay in our peaceful one bedroom black bear themed unit. Cozy living room with games, smart tv, wifi, dvd player and movies. Great work space in bedroom. Unit has a full kitchen, full bath. Enjoy axe throwing, shoot some hoops or sit by the campfire (pending fire bans in drought conditions.) Hike to the brook and enjoy our trails on 15 acres. Check out our guidebook for ideas on tons of local dinning and activities. Min from Hopkinton/Everett trail system and Clough state park.

Downtown Derry, Studio Apartment
Cozy up during your next trip to southern NH! Built in 1910, the home has been completely renovated. The Studio is a combination of elegance and comfort from the walls of windows that flood the space with light and scenic conservation/golf course views to the spacious backyard that is perfect for a peaceful escape. It is 5 minutes from i-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Cozy Central Downtown 2BD Unit Close to 93 & Elm
Enjoy this stylish space at this centrally located apartment right in downtown Manchester, designed for you and your family to relax, and enjoy what New Hampshire has to offer. We designed this space to accommodate your everyday needs as well as please the eye. Located on a very busy/noisy street. ✓ 2 Mins to downtown Elm Street ✓ 3 Mins to Interstate 93 ✓ 5 Mins to the Elliott Hospital ✓ Tons of things to do/eat close-by ✓ Free on-site parking ✓ Easily Accessible ✓ Private Entrance

Charming House on 7 Acres in Rural New Hampshire
This magical place has been our home away from home for twenty years and we are excited to share it with you. We hope you'll experience the same time-out-of-time feeling we get when sitting out on the deck in the early morning or looking up on a moonless night as the Milky Way snakes its way across the dark sky. The house sits on seven mostly wooded acres that abut a scenic beaver pond. The property is located on a quiet unpaved road in rural New Hampshire.

Woods n’ Wetlands Studio
Welcome to Woods’n’wetlands located in beautiful New Boston NH. Enjoy late night fires, beautiful scenic walks, skiing and snowboarding or some of the beautiful local shops. When you are at Woods’n’wetlands you will be at peace. When you step outside you can hear the stream flowing, the birds chirping and the frogs singing. At night you look up to the stars and during the day you walk out to a beautiful yard. Steps away you can enjoy your private fire pit.

Welcome to Merry Hill!
Take a break and unwind at Merry Hill - a peaceful wooded oasis. Merry Hill is located in Greenfield, NH about 10 minutes away from Crotched Mountain for skiing and hiking. We are mid-point between Keene and Manchester. Your private, separate entrance guest suite includes: • Queen Bed with 14” Memory Foam Mattress • Full Bathroom with Tub and Shower • Complimentary Shampoo, Conditioner & Body Wash • Mini-Fridge with Coffee / Tea Station

Spacious Souhegan Getaway
We would be happy to welcome you to our spacious walk-out basement apartment that features a comfortable and stylish living space. The apartment decor is warm and contemporary, with a large living and eating area, modest kitchenette, bedroom with queen size bed, and fully appointed bathroom. We are close to downtown Milford and 30 minutes from Nashua and Manchester, as well as an easy drive to Merrimack Premium Outlets.
Popular amenities for Hillsborough County holiday rentals
Other great holiday rentals in Hillsborough County

Bee Haven - Room #3

Lovely private space with a view

The Lions Share Master Bedroom

Lake house Overlook

Bright Bedroom with Queen bed

Spacious Basement Retreat for the Solo Traveler

Private Guest Suite Near Downtown Peterborough

Comfortable and cozy room with a private bathroom.
Destinations to explore
- Rentals with outdoor seating Hillsborough County
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- Apartment rentals Hillsborough County
- Hampton Beach
- Fenway Park
- TD Garden
- Boston Common
- Harvard University
- Revere Beach
- Lynn Beach
- Monadnock State Park
- New England Aquarium
- MIT Museum
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Museum of Fine Arts, Boston
- Jenness State Beach
- Quincy Market
- Pats Peak Ski Area
- Rye North Beach
- North Hampton Beach
- Prudential Center
- Salem Willows Park
- Franklin Park Zoo
- Symphony Hall
- Boston Children's Museum




