Vacation rentals in South Milford

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Top-rated vacation rentals in South Milford

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A comfortable living room is showcased with a fireplace surrounded by elegant marble. Soft gray sofas are arranged around a central coffee table featuring decorative elements. Warm lighting is provided by floor and table lamps, creating a welcoming space for relaxation.

Home in Manchester

Residence of Manchester

Relax with the whole family at this spacious, traditional home overlooking a conservation area. Enjoy the large outdoor deck equipped year round with a propane grill. Experience the fresh air of spring, the gorgeous reds and oranges of autumn, or the novelty of winter and its holidays from a house that does them all! The Residence is just outside the hustle and bustle of the City but minutes away from Manchester Airport and Mall of NH with its array of shopping, restaurants and entertainment.

ValueFamilyComfort

4.96 out of 5 average rating, 120 reviews

Top guest favorite

Loft in Lyndeborough

European Style Loft • Autumn Colors • Dog-Friendly

The Loft is a refined European-style countryside retreat set on 20 private acres of meadow and forest in the heart of New Hampshire’s autumn beauty. Wake to misty mornings and coffee overlooking changing leaves, wander woodland trails with your dog, watch deer at dusk, and return to cozy evenings and brilliant stargazing through expansive windows. Quiet, private, and thoughtfully designed for couples or close companions seeking calm, comfort, and a slower pace. Calm, well-behaved dogs welcome.

LocationValueOutdoor spaces

4.99 out of 5 average rating, 85 reviews

Top guest favorite

A quaint cabin sits amidst lush greenery, framed by tall trees. The blue exterior features a welcoming porch, flanked by blooming white hydrangeas. A well-kept lawn complements the serene landscape, providing a peaceful retreat in a natural setting.

Guesthouse in New Ipswich

"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)

ValueFamilyCheckout

4.95 out of 5 average rating, 428 reviews

Top 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

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.

LocationValueSkiing

4.94 out of 5 average rating, 689 reviews

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

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!

ValueLocationBathroom

5.0 out of 5 average rating, 187 reviews

Guest favorite

A modern ranch-style home is set against a backdrop of lush greenery, featuring a combination of wood and large glass windows. Solar panels are visible on the roof, with a stone wall and landscaped area framing the exterior. The property blends harmoniously with the surrounding nature.

Home in Amherst

Modern Luxury in a Spectacular Natural Setting

The Pond House is a hidden gem: A Frank Lloyd Wright-inspired modern ranch on 6 acres, with a private pond. Equal parts modern architecture and natural beauty, our secluded property is the perfect place to unwind in solitude, or use it as a base for local adventures. Under vaulted ceilings, endless windows and the screened porch offer seamless indoor-outdoor living in a stylish space. Explore the woods on our 1/4 mile of private paths, or enjoy a campfire at the edge of our private pond.

ValueFamilyView

4.97 out of 5 average rating, 99 reviews

Guest favorite

Home in Milford

Colonial Cape Home

Step back in time and enjoy a stay in this historic 1746 colonial home, just two miles from the town Oval. Experience the character of early American life with original features like the cooking fireplace, extra-wide floorboards, and countless preserved original details. Whether you're a history enthusiast or simply looking for a unique getaway, this one-of-a-kind home offers a true taste of colonial living with modern comfort. Please read the "Other details to note" before booking.

LocationValueHospitality

4.88 out of 5 average rating, 25 reviews

Top guest favorite

A rustic cottage is situated among lush greenery, with a well-maintained pathway leading to the entrance. The exterior features a combination of wood and stone elements, complemented by a large tree providing shade. The serene lake is visible in the background under a bright blue sky.

Cottage in Weare

Lakeside cottage. Gorgeous view & several boats.

Come and enjoy a relaxing stay at our peaceful cottage on Daniels Lake. The small, recently-renovated home is in a rural setting but close to restaurants, shopping, parks, ski slopes, golf courses, lakes and quaint New England villages. The large deck has a gorgeous view of the lake. Four kayaks, two canoes, standup paddle board and pedal boat are available to use on the lake which is known for its good fishing. Two bedrooms, dining room and living room overlook the lake and woods.

ValueLocationCheck-in

4.97 out of 5 average rating, 150 reviews

Top guest favorite

A modern home features a combination of dark siding and natural wood accents, positioned among tall trees. A welcoming porch extends from the entrance, complemented by an American flag. The surrounding area includes a gravel path and vibrant greenery, providing a serene atmosphere.

Home in Jaffrey

Willow Falls Home ~Hot tub & Waterfront

Constructed waterfall views are just feet away from you! Not far from Boston, RI or CT, this newly designed home is located at a privately viewed pond, in New England, near Mt. Monadnock! Kick back, relax & listen to the water falling in a screened-in gazebo, or in the outdoor hot tub! Or view it all at the picture windows and enjoy the solitude at this picturesque retreat! Inside you'll find multiple lounging areas, luxurious beds, a fully stocked kitchen and a fun game room.

LocationValueAmenities

4.98 out of 5 average rating, 106 reviews

Top guest favorite

A bright yellow two-family home is positioned amidst greenery, featuring a welcoming entry with a red door. A small flowering tree adds a splash of color in front, while a large deck is visible in the background, perfect for outdoor gatherings.

Home in Chelmsford

Newly renovated, spacious, clean, 3 bedroom home.

Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

FamilyLocationCleanliness

5.0 out of 5 average rating, 259 reviews

Guest favorite

The spacious bedroom features a large bed with neatly arranged linens. Two bedside lamps illuminate the space, while a cozy chair is positioned in the corner. Light-colored walls complement the wood-like flooring, creating a calm and airy atmosphere.

Apartment in Amherst

Lovely 2 Bedroom entire apartment in Amherst.

Lovely 2 bedroom entire apartment. Newly renovated in a convenient location. Right on the center of all local activity on route 101A. One bedroom with King size bed and another bedroom with a Queen size bed. A Large living room area with an extra sofa-bed to accommodate up to two additional people. And finally a kitchen with appliances and a dining area for four people. NEMA 14/50 outlet is now available for our guests with EV. Extra guest fee: after 2 guest, is $10 per night.

LocationFamilyCleanliness

4.81 out of 5 average rating, 117 reviews

Guest favorite

A serene quarry landscape is captured, featuring a calm body of water surrounded by lush greenery. A floating platform is visible on the water, along with a small dock in the distance. An American flag adorns the rocky shoreline, adding to the natural beauty.

Home in Milford

Beach~Lake~Hot Tub~Kayaks~Paddle Boards~Swimming

Your granite quarry sanctuary awaits. Beach House overlooks the private beach entrance to crystal-clear mineral waters. Unwind under the stars in our year-round hot tub. Sun-soaked living room with gas fireplace, game room with movie theater and arcades, kids bunk beds & swing. Walk to restaurants, 30min drive to skiing, hiking trails throughout. Wake to ancient stone vistas, swim, and relax. Where granite heritage becomes your family paradise

FamilyLocationGetting around

4.88 out of 5 average rating, 80 reviews