Holiday houses in Medfield

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Top-rated holiday rentals in Medfield

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Top Guest favourite
The exterior of a two-level home is depicted, surrounded by lush green lawns and mature trees. A pathway leads to the welcoming entrance, flanked by garden beds featuring various plants. The house features a traditional design with large windows allowing for ample natural light.
Home in Holliston
4.97 out of 5 average rating, 110 reviews

All New Private Country Setting (2 Level-No Share)

We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

Top Guest favourite
A charming farmhouse stands amidst a lush garden, surrounded by vibrant purple irises. The white exterior of the house contrasts beautifully with the greenery, providing a serene atmosphere. Tall trees and a manicured lawn enhance the inviting landscape of the property.
Guest suite in Weston
4.99 out of 5 average rating, 183 reviews

Flower Farm Getaway 2BR, 20 Min To Boston

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

Top Guest favourite
A view of the calm water on Mirror Lake is framed by a flower-lined, stone patio leading to a wooden dock. The water reflects the greenery from the surrounding trees under a clear blue sky.
Home in Wrentham
4.96 out of 5 average rating, 94 reviews

Relaxing Waterfront Lake House, 10 min to Gillette

Relax at this peaceful, family-friendly lake house on Mirror Lake. Fully renovated 3-bedroom, 2 full bath getaway directly on the water with private deck, dock, patio area, propane grill, paddle boards, kayak, fishing, and more. Located nearby Gillette Stadium, Patriot Place, Wrentham Premium Outlets, Plainridge Park Casino, an abundance of restaurants, wedding venues, walking trails and central to Boston or Providence, this is a great location for many activities or just lounging by the water.

Top Guest favourite
A serene bedroom suite features a spacious bed with a light blue quilt, flanked by two windows allowing natural light. A cozy sitting area includes a comfortable couch with patterned pillows, and decorative rugs are placed on the hardwood floor, enhancing the inviting ambiance.
Guest suite in Dover
4.97 out of 5 average rating, 302 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stair climbing required to reach bedroom suite.) I welcome quiet, mature guests as this is a very peaceful (non-party)environment. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling. I have owned and loved this home for 35 years and take great joy in its charm and outdoor spaces.

Top Guest favourite
The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.
Guest suite in Sharon
4.97 out of 5 average rating, 211 reviews

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

Guest favourite
The exterior of the building features a unique blend of brick and siding, with a striking orange bottom section. Windows are placed symmetrically, allowing for natural light. A garage door is visible, along with a set of steps leading to the entrance, framed by a well-kept area.
Guest suite in Franklin
4.87 out of 5 average rating, 176 reviews

Cozy, Cute & Charming In-Law Apt w/Private Access

Cozy, Cute & Charming In-Law Apt w/ Private Access & Parking in Franklin City Center. Everything is within walking distance. It’s perfect for couples, solo adventures and business travelers. Just minutes walk to Train Station, Shopping Centers, Restaurants, Museum, Theater House, Libraries, Dean College, Trail & Tracking. Few minutes drive to Gillette Stadium, Wrentham Outlets, Xfinity Center, Boston Marathon Starting Point. You can easily visit Boston, Providence, Newport & Worcester, too!

Top Guest favourite
A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.
Place to stay in Sherborn
4.98 out of 5 average rating, 322 reviews

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

Guest favourite
A renovated kitchen features modern cabinetry and a sleek countertop. Stainless steel appliances, including a dishwasher, are present. Distinctive hardwood flooring adds warmth to the space, while natural light illuminates the area through nearby windows.
Apartment in Millis
4.89 out of 5 average rating, 18 reviews

Small Town 3BR in heart of Millis

Millis is a small community, but with this apartment you are in the heart of it! Walk up to the 2nd floor of this building and enjoy 3 bedrooms, hardwood floors, renovated kitchen and bath, and even a private laundry in the basement. Steps from 7 restaurants, public library grounds, spas, and coffee/tea shops is like city living in a small New England community. Short drives to Gillette Stadium in Foxboro, Commuter Rail station in Norfolk, and Outlet Shopping in Wrentham.

Guest favourite
A stylish wooden bed frame with a floral-patterned comforter and two pillows is featured in the sleeping area. A bedside table with a lamp stands next to the bed, and a wooden dresser is positioned nearby against the wall.
Apartment in Framingham
4.96 out of 5 average rating, 304 reviews

Comfortable apartment in Framingham

Newly renovated basement apartment. Private entrance and living space which includes a kitchen, bedroom, hallway and bathroom. The kitchen has a microwave and refrigerator, but no stove. Very clean and well maintained. Comfortable queen size bed. Driveway space for 1 car and plenty of street parking. Great location. Walking distance to Dunkin' Donuts, Domino's Pizza, and local shops. Less than 2 miles from the Mass Pike. No Pets / No Smoking inside

Guest favourite
A well-lit bedroom features a spacious bed adorned with patterned bedding. Natural light filters through two large windows with wooden blinds, illuminating the soft carpeted floor. A bedside lamp provides additional warmth, and a door is partially visible on the right.
Guest suite in Wellesley
4.81 out of 5 average rating, 337 reviews

Private suite 1 BR, 1 BA, 1 LR, 1FLR

Prime location in Wellesley Hills, MA. Garden level suite offers a living room and a bedroom with a private bath. It offers a full size bed in the bedroom and a queen size pullout sofa in the living room. Private entrance with smart lock entry. Easy access to commuter rail, restaurants, post office, bank, Babson College, Wellesley College and Olin College of Engineering and so much more.

Top Guest favourite
A comfortable seating area is highlighted by two stylish armchairs and a soft sofa. Natural light filters through large windows that overlook the greenery outside. A modern rug is placed on the wooden floor, complementing the decor, while a lamp and coat rack add functional touches.
Home in Framingham
4.97 out of 5 average rating, 100 reviews

Cozy en suite w/ high ceilings

Enjoy this peaceful oasis with backyard views of the tall pine forest and soothing sounds of a patio waterfall. Private entrance en suite features off street parking, air conditioning, easy access to major amenities. 10 minutes to Mass Pike. 5 minutes to Framingham State University.  Very safe and easily walkable neighborhood. Use of propane fire pit upon request. 

Top Guest favourite
A leather recliner sofa is positioned in a light-filled living area, complemented by a large painting of a serene landscape. A full-size refrigerator and a TV stand are visible, providing essential amenities. An entryway is seen in the background, leading to additional rooms.
Guesthouse in Framingham
4.97 out of 5 average rating, 312 reviews

Private guest house on beautiful country road

Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.

Popular amenities for Medfield holiday rentals

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