Holiday rentals 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

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

We built this 2 level home 9 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.

LocationValueCheck-in

4.97 out of 5 average rating, 144 reviews

Top guest favourite

Guest suite in Dover

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.

LocationFamilyGetting around

4.98 out of 5 average rating, 346 reviews

Guest favourite

A well-maintained yard sits on a spacious acre, featuring lush green grass and a variety of trees. The house is partially visible on the right, and a clear path leads to the sunroom entrance. Flower beds with blooming plants add color to the landscape.

Home in Walpole

Entire home 3 miles from Gillette, sleeps 7.

Large yard, great for pets, this 3 BR/5 bed, well maintained home is situated 30 Minutes to Boston & Providence RI, 3 miles to Gillette Stadium & the commuter rail. Home is surrounded by many Pine trees, set back from the main road, on corner of a Cul de Sac good for walking and peace and quiet. Everything you need should be there, this was family's private residence now an Airbnb. Sit back & relax in the yard listening to the birds & enjoying nature all while being minutes to everything!

ValueLocationGetting around

4.89 out of 5 average rating, 114 reviews

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

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.

LocationFamilyLayout

4.96 out of 5 average rating, 235 reviews

Guest favourite

Home in Framingham

Retreat Near Boston | AC, BBQ, Deck, Pets OK

Welcome to your perfect home base just outside Boston—ideal for families, groups, and business travelers alike. This bright and spacious 4-bedroom home comfortably accommodates your group with 5 beds and plenty of room to relax. Enjoy a fully fenced in backyard. Enjoy a large, sun-filled living area, a bonus dining space with beautiful vaulted ceilings, Kawaii Piano, and a fully equipped kitchen with modern stainless steel appliances—perfect for gathering and entertaining.

FamilyLocationQuiet

4.92 out of 5 average rating, 12 reviews

Guest favourite

Flat in Millis

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.

ValueFamilyNearby

4.88 out of 5 average rating, 42 reviews

Superhost

Home in Norwood

4br Near Stadium | Hot Tub + Firepit

Welcome to The Trophy House — your home base for fall in New England. Catch a Patriots game at nearby Gillette Stadium, spend a crisp day exploring Boston, or simply enjoy the season from the bright porch. Come home to golden-hour drinks in the patio courtyard, gather around the firepit as the air cools, then end the night soaking in the hot tub under the stars. With 4 bedrooms and room for 8, it’s made for memorable fall weekends with family and friends.

LocationFamilyAmenities

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Flat in Walpole

Walk to Gillette Stadium | Sleeps 6 | Parking

Stay just 1.5 miles from Gillette Stadium & Patriot Place—an easy 25–35 min walk to games, concerts, dining & events. Park free in our off-street spaces, then walk straight to the stadium or take a quick rideshare. This spacious 2-level, 2-BR apartment sleeps 6 with a full kitchen, in-unit washer/dryer, fast Wi-Fi, A/C & private patio with grill. Located in a quiet residential neighborhood, the perfect comfortable home base just minutes from the action!

FamilyLocationAir conditioning

5.0 out of 5 average rating, 14 reviews

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

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. NEW in 2022: Mini-split AC!

FamilyValueSolo travel

4.98 out of 5 average rating, 360 reviews

Guest favourite

The exterior of the house is shown at dusk, featuring a two-story design with a mix of gray siding and white trim. Soft lighting highlights the entrance and landscaping along the front, while a large grassy area is visible in front of the home.

Townhouse in Norwood

Family Vacation Modern Home

Our home is in a quiet and family-friendly neighborhood, yet still offers easy access to the vibrant city as well as the surrounding natural beauty. Enjoy the many next door restaurant within waking distance : Texas Road house , Panera Bread, Five Guy Burger, McDonald. Taco Bell , Panda Express and chili's. Wapole Mall : Kohl’s, Old Navy. Barnes and Noble , Joann Ann Fabric, T-Mobile , Party City and Five Below, and Aldi.

LocationValueHeating

4.97 out of 5 average rating, 59 reviews

Superhost

Home in Sharon

Luxury 4BR Near Gillette | Games + Firepit

Welcome to The Sharon Farmhouse—walk to town for coffee and breakfast at Angel’s Cafe, then spend the day exploring Boston by train, relaxing at Lake Massapoag, or heading to Gillette Stadium for a game or concert. Return home to ping pong or foosball, and evenings around the firepit. Perfect for 10 guests (9 adults max) - 2 large families or groups, with plenty of space to gather, unwind, and make memories together.

FamilyLocationCleanliness

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Franklin

Home Near Gillette Stadium

Bring the whole family to this great place with lots of room for fun. This large and flexible living space will amaze you around every corner. Conveniently located near Gillette Stadium, shopping, Rt 495, Dean College, and the commuter rail. You're going to love staying at this property. Gillette Stadium - 13 miles Xfinity Center - 15 miles Wrentham Outlets - 12 miles Starbucks - 0.5 miles Grocery Store - 0.7 miles

LocationFamilyAccuracy

4.97 out of 5 average rating, 31 reviews