Vacation rentals in South Milford

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Top-rated vacation rentals in South Milford

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Guest favorite

Guest suite in Windham

4.99 out of 5 average rating, 260 reviews

Sunny, private and peaceful apartment!

Our home sit in a private and peaceful setting. It is perfect for the business travelers looking for a place to relax at the end of the day or anyone looking for a quiet place. Close to Castleton Banquet and Conference Center, Searles Castle, Canobie Lake Park, walking & biking trails, shopping and restaurant. Centrally located between Boston, beaches and mountain and lake region. Only 16 miles from Manchester Boston Regional Airport, 36 miles from downtown Boston, 3.5 miles from Interstate 93.

Guest favorite

Guest suite in Deering

5 out of 5 average rating, 259 reviews

Elegant Lodging in the Woods ~Privacy & Comfort!

Come relax and unwind in this nicely appointed secluded, guest suite. Privacy guaranteed in this smoke free “home away from home”. Country, wooded setting surrounded by Pat's Peak, Crotched Mtn. Mt. Sunapee, skiing, hiking, lakes, & golfing. Convenient location for day trips to the seacoast, Concord or Peterborough. Cozy cathedral ceiling bedroom/living room studio, private bathroom, kitchenette/workroom. Super clean! Private locked entrance. FREE onsite parking. Only 75 minutes from Boston.

Guest favorite

Cottage in Petersham

4.99 out of 5 average rating, 179 reviews

Cider House Cottage

Antique guest cottage on a country 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

Guest suite in Ashburnham

4.98 out of 5 average rating, 436 reviews

The Ginger Bed King Suite

Come for the lovely country setting, the winter beauty, amenities, neighborhood, convenience, privacy, spaciousness, and the comfortable bed. Close to many wonderful hiking/biking paths, rail trails, Wachusett ski area, Jewel Hill, Lake Wampanoag, Kirby area. WI-FI, TV ( Hulu and Netflix), refrigerator, microwave, coffee/tea maker, reading lights, table area, continental breakfast, parking... Good for couples, solo and business travelers. (Key pad for Covid safe entry) Everyone is welcome!

Guest favorite

Guesthouse in Wilton

4.95 out of 5 average rating, 622 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.

Guest favorite

Guest suite in Merrimack

4.86 out of 5 average rating, 143 reviews

Mini-Apartment in Quiet Neighborhood

Located in a quiet, secluded neighborhood, yet only 15min from Nashua and Manchester--you'll be close to everything, yet away from it all. This is the perfect spot for business travelers, short-term medical professionals, or vacationers looking to experience NH. This peaceful spot has access to hiking trails, lakes, Merrimack Outlets, and more. Hosts are a friendly couple happy to provide any recommendations you need! PLEASE NOTE: You will hear active children upstairs during daytime hours.

Guest favorite

Guest suite in Merrimack

4.99 out of 5 average rating, 192 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.

Guest favorite

Loft in Peterborough

4.99 out of 5 average rating, 142 reviews

Peaceful Mill on the Water - Home Away from Home

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.

Guest favorite

Guesthouse in New Ipswich

4.95 out of 5 average rating, 332 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!

Guest favorite

Guest suite in Peterborough

4.99 out of 5 average rating, 143 reviews

Meadow View

Explore our sunlit sanctuary in a 275-year-old farmhouse. Our 'in-law' suite is a cozy retreat, full of light and art. Adjacent to Casalis State Park, enjoy scenic trails for biking, hiking at all seasons. Enjoy Peterborough's charming yoga studios, coffee shops and restaurants. Meadow View offers a 750 sq ft private suite with a king-size bed, clawfoot bathtub, and a mini kitchen. Your comfort is our priority. Experience the perfect blend of historic charm and comfort.

Guest favorite

Guest suite in Hollis

4.97 out of 5 average rating, 139 reviews

Pine Estate - Private suite

Welcome to our spacious guesthouse located - 2 miles from Nashua - 5 minutes drive to the highway - 40 minutes to Boston and minutes from Hollis. Hollis is an active farming community offering beautiful orchards, nature paths, art studios and a winery. Beautiful private yard with a large patio where you can relax and enjoy nature at its best. Our place is ideal for a weekend get-away or business travelers. Please note there will be no exception to the no pets policy.

Guest favorite

Tiny home in Orange

4.92 out of 5 average rating, 346 reviews

The Writer's Retreat: A Sweetwater Stay

Located on the shore of Tully Pond, The Writers Retreat is a newly designed 325sqft lake side cottage with breathtaking views of Tully Mountain. This 4-season cottage is built with salvaged barn wood; up-cycled maple floors and custom built furniture and lighting. It's the little sister to The Fishing Cottage. You'll find this intimate home has everything you need to relax, write the next Great American Novel, connect with a lover, or just plain chill.