Vacation rentals in South Milford

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Top-rated vacation rentals in South Milford

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Top guest favorite
An outdoor tub is situated on a wooden deck, surrounded by vibrant autumn foliage. A red faucet provides a natural flow of water, while a small bowl of floating objects rests nearby. In the background, a glimpse of a serene lake can be seen through the trees.
Cabin in Stoddard
4.98 out of 5 average rating, 128 reviews

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.

Top guest favorite
A serene pond reflects the white cottage and surrounding trees, creating a tranquil scene. Wildflowers and grasses frame the water's edge, while lush greenery enhances the natural beauty of the area. The peaceful environment is ideal for relaxation and outdoor exploration.
Cottage in Petersham
4.99 out of 5 average rating, 227 reviews

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Guest favorite
A bright red treehouse is nestled among snow-covered trees, showcasing holiday lights around its round window. A snow-dusted wooden boardwalk leads to the entrance, surrounded by a serene winter landscape filled with evergreens.
Treehouse in Dunbarton
4.93 out of 5 average rating, 1,104 reviews

Treetop Sanctuary

Get away from life at the treetop sanctuary! Follow the suspended path through the trees to your own little treetop oasis. This standalone space rests 30 feet above the forest floor. The space is perfect for reconnecting with nature. Amenities: Elec. WIFI, Compost toilet, Woodstove, Fridge. Bring; *SLEEPING BAGS* or Blankets/Linens (queen size) Pots and pans, (If You wish to cook on the stove) Accepting children 10 +up. Absolutely no pets. During winter months only accepting guests with 4wd.

Top guest favorite
Guesthouse in New Ipswich
4.95 out of 5 average rating, 395 reviews

"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)

Top guest favorite
Guest suite in Fitzwilliam
4.95 out of 5 average rating, 364 reviews

The Carriage House in Historic Fitzwilliam

Welcome to the Carriage House! Former site of the popular Hannah Davis House Bed and Breakfast, this gorgeous space is ready for your visit! Beautiful wood beams throughout, a cozy loft bedroom, and a completely separate entrance for privacy. Short rides to Rhododendron State Park, Mount Monadnock, Gap Mountain, the Cheshire Rail Trail, Laurel Lake, and many more outdoor activities year round. Walking distance to the town common in a town where little has changed and history is preserved.

Guest favorite
A cascading waterfall flows over natural rocks, surrounded by lush greenery. Delicate pink flowers in the foreground enhance the serene setting, where the sound of rushing water and natural beauty create a peaceful atmosphere.
Guesthouse in Wilton
4.94 out of 5 average rating, 668 reviews

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.

Top guest favorite
A spacious living area features a gray sofa and a patterned armchair, accompanied by a wooden coffee table. A small table holds a lamp and magazines. A doorway leads to the bedroom, while a kitchenette is visible in the background.
Guest suite in Merrimack
4.99 out of 5 average rating, 267 reviews

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.

Top guest favorite
The studio features a spacious bed with white linens, accented by decorative throw pillows. A vibrant piece of art adorns the wall above the bed. A modern vanity area with a sink is visible, along with natural light filtering through windows that offer views of the surrounding woods.
Guest suite in Milford
5 out of 5 average rating, 151 reviews

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!

Top guest favorite
An inviting open living space showcases warm brick walls and original timber beams. A spacious seating area features a brown leather couch and wooden coffee table, while a grand piano occupies one corner. Large windows with serene views of the outdoors offer natural light.
Loft in Peterborough
5 out of 5 average rating, 216 reviews

Top 1% Property - Peaceful Mill with Waterfall

Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated workspace.

Top guest favorite
A cozy living area features a dark upholstered couch and wooden dining furniture set for four. Natural light enters through a skylight and a window, illuminating the space. A patterned rug lies beneath a coffee table surrounded by books and games, enhancing the inviting atmosphere.
Guesthouse in Dunbarton
5 out of 5 average rating, 146 reviews

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.

Top guest favorite
The exterior of a cozy house is illuminated by warm lights during twilight. Snow blankets the ground and roof, while bare trees stand around the property. The entrance features a welcoming glow, suggesting a comfortable atmosphere inside.
Home in Greenfield
4.94 out of 5 average rating, 171 reviews

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.

Top guest favorite
A welcoming sleeping area features a queen bed dressed in navy bedding, complemented by two bedside lamps. A decorative pillow adds an accent to the bed. Textured area rugs are placed on the hardwood floor, enhancing the cozy atmosphere of the room.
Guest suite in Greenfield
4.95 out of 5 average rating, 147 reviews

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

Popular amenities for South Milford vacation rentals