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Holiday rentals in Medway

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Top-rated holiday rentals in Medway

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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, 115 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 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, 306 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 Victorian home is showcased, featuring a light-colored facade with decorative trim. A welcoming porch area is accented by potted plants, and steps lead up to a wooden front door flanked by tall windows. Lush greenery surrounds the property.
Flat in Newtonville
4.87 out of 5 average rating, 560 reviews

Country Charm minutes from the Hub - 1st Floor Apt

Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

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, 103 reviews

Cozy en suite w/ high ceilings

 Relax in this peaceful private en suite with breathtaking backyard views of the tall pine forest. Lots of natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. 25 min to Boston. 30 min. to Foxboro Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

Top guest favourite
A fully equipped kitchen is shown, featuring stainless steel appliances including a refrigerator, microwave, and dishwasher. Granite countertops provide ample workspace, while natural light filters through the two windows above the sink. A coffee maker sits on the counter, adding to the amenities.
Home in Framingham
4.9 out of 5 average rating, 255 reviews

1BR—Bright & Cozy 2-Level Place — 25 Min to Boston

800ft² 1-Bedroom, 2-Level Apartment Private Rental @ our 3-Rental Property 1st Floor: —Fully Equipped Granite Kitchen w/Dishwasher + Essentials & Cookware —Living Room w/Queen Sofa Bed + Dining Table 2nd Floor: —Bedroom - Memory Foam Queen Bed —Full Length Mirror —Desk & Chair + Dresser —Bathroom - Shower/Tub Backyard Patio Laundry Room (Basement) Driveway Parking 25 min to Boston 15 min walk to Train 5 min walk to Jack’s Abby Brewery 3 min walk to Park/Playground Deep Cleaned & Sanitized

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, 330 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!

Top guest favourite
The kitchen area features white cabinetry and a light countertop, equipped with a microwave, dishwasher, and a compact refrigerator. A cozy seating nook by the window includes a modern black chair and a small table, with a patterned rug adding warmth to the space.
Flat in Downtown Providence
4.98 out of 5 average rating, 101 reviews

Walking Distance to RISD, Brown, & Convention Hall

Historic charm in downtown Providence! Enjoy restaurants and attractions within walking distance! Conveniently located in the heart of DownCity, and less than a half mile from Brown University, you'll enjoy endless dining options in one of America's top 10 foodie cities. Take a quick walk over to the East Side to experience Providence's historic culture while walking the grounds of Brown University. Whether you're staying a week or a month you will have endless options to explore in PVD!

Top guest favourite
A charming historical two-story house features a gray exterior with dark trim, complemented by vibrant flower beds in front. The main entrance showcases a bold red door, flanked by several windows that illuminate the inviting facade.
Guest suite in Uxbridge
4.98 out of 5 average rating, 121 reviews

Privacy & Peacefulness @ Emerson Brook

A 2nd floor separate entrance and self-checkin / checkout make this your perfect getaway in Blackstone Valley (halfway between Worcester and Providence RI). A private deck and 400 sf of space - kitchen, bedroom, dining, living room and great work space - is all yours. The bathroom includes a clawfoot tub/shower. Expect a Keurig (with k-cups), great linens, wifi, cable and smart tv. Sit on your deck, grab a drink, relax and enjoy the sound and views of Emerson Brook Farm...

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.
Flat in Millis
4.9 out of 5 average rating, 20 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.

Top guest favourite
A modern living area features a gray sectional sofa adorned with patterned cushions and a yellow accent pillow. A round wooden coffee table sits in front, accompanied by a small potted plant. Art pieces with vibrant colors are positioned on the white brick walls, enhancing the space.
Flat in Federal Hill
4.94 out of 5 average rating, 366 reviews

Modern space off of DePasquale SQ in Little Italy

Welcome to our modern and cozy city apartment on a commercial street w/parking, less than a mile away from Downtown Providence! Walking distance to Broadway St, West Fountain commercial corridor, and Providence's west Side. We hope our renovated unit, equipped with a new bed, G-Home mini speaker, projector (stream your favorite shows, movies and more, directly from your personal devices) + other amenities will make for a comfortable, and enjoyable experience!

Guest favourite
A heart-shaped hot tub is nestled beside a sparkling swimming pool. The clear water reflects the surrounding greenery. A dog rests comfortably on the edge of the hot tub, observing the tranquil scene. Loungers are positioned nearby for relaxation.
Flat in Holliston
4.93 out of 5 average rating, 134 reviews

Lake Link

Beautiful fully stocked 2 BR apartment located in Holliston Historic District. Top of the line swimming pool with waterfall and hottub (May 31-Sep 30). Full kitchen, full bath, washer/dryer, central heat and AC, fireplace, wireless internet, Cable TV with almost all premium channels available, private driveway and entrance. Sorry, but no pets allowed. Note: COVID19- We require all eligible guests to be vaccinated or have 72 hr negative test.

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.
Guest house in Framingham
4.97 out of 5 average rating, 317 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 Medway holiday rentals

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Norfolk County
  5. Medway