Holiday rentals in Milton

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Top-rated holiday rentals in Milton

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Guest favourite

Guest suite in Dorchester

4.92 out of 5 average rating, 118 reviews

Boston arbor oasis - cute one bedroom suite

Upbeat, beautiful one bedroom with attached bathroom. Have the ground floor / lower level of our home to yourself. Your own private entrance, come and go as you like. Located on a quiet, dead end street in a very safe, residential Boston neighborhood, with big beautiful evergreen trees. Convenient to 93. Five minute Uber or short bus ride to Ashmont station, from here take the train downtown Boston. Free off street parking. Easy walk to coffee shops, restaurants, bars, and Neponset River trail!

Guest favourite

Guest suite in Dorchester

4.96 out of 5 average rating, 227 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A truly unique master bedroom and a cozy 2nd bedroom both adjacent to a marble spa bathroom (which has a heated floor and a large shower with a built in bench). With a clean, glass-tiled kitchen with granite-top counters, you'll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood perfect for romantic couples, solo adventurers, and savvy business travelers who want the feel of a downtown hotel without the high price.

Guest favourite

Guest suite in Jamaica Central - South Sumner

4.92 out of 5 average rating, 214 reviews

Cozy Private Garden Studio near the Heart of JP

Best of both worlds: this airy and light, newly renovated private studio is set in a beautiful, secluded backyard/garden. Easy walk to restaurants, shops and acres of green space. Your reservation confirms that you have read "Other Things to Note" in The Space section below and "House Rules" before booking. Guests can only book for themselves. We are 5-7 minutes from the 39 bus and 15 from the Orange line. There is a microwave, fridge, counter and and sink but no stove or cooking options.

Guest favourite

Guest house in Scituate

4.93 out of 5 average rating, 100 reviews

Serenity House

Take a deep breath while relaxing on this 1+ acre wooded estate surrounded by the Hubbell Woodland Preserve and the Hatherly Golf Course across the street. Walk along seaside estates that greet you on your way to swim at Minot Beach which is a short walk away. Ride your bike to Cohasset Harbor while taking in the view of the fishermen catching lobsters and have dinner at the local restaurants. Listen to the waves and smell the salty ocean air and relax and sleep peacefully at Serenity House!

Guest favourite

Home in Hyde Park

4.91 out of 5 average rating, 318 reviews

~*30min to Downtown*~ THE COSMOPOLITAN

Stylish contemporary kid-friendly apartment on the first floor of a multi-family. Bright and roomy bedrooms with a large eat-in kitchen. Central air conditioning. Plenty of free street parking. Access to shared laundry room. Located in Hyde Park neighborhood, 30 minute drive into downtown Boston. Professionally cleaned and disinfected. Room 1: Queen size bed, closet, TV Room 2: Queen size bed, closet Room 3: Living room couch bed, closet, TV Entryway: Includes Mrs. Pac Man wall arcade

Guest favourite

Home in Quincy

4.97 out of 5 average rating, 143 reviews

Artist's Haven (2)

Explore Quincy/Boston from my artistic retreat! Before booking, please research the area to ensure it's ideal for you. As a Superhost, I strive to deliver a 5-star experience. Experience a vibrant, artsy, and tranquil environment that mirrors my passion for art. This immaculate, peaceful 1-bedroom apartment on the 2nd floor is crafted for a perfect energy flow—a sanctuary of creativity, designed, and adorned with my original artworks, adding a unique and inspiring touch to every corner.

Guest favourite

Guest suite in Dover

4.97 out of 5 average rating, 233 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-stairs climbing required to reach bedroom suite.) I welcome quiet, mature guests. 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, and surprisingly close to downtown Boston. I have owned and loved this home for 33 years and take great joy in its charm and outdoor spaces.

Guest favourite

Rental unit in Dedham

4.91 out of 5 average rating, 133 reviews

Prince Charming Suite *near Boston* sleeps 4-5

As you approach this non-smoking property, you will have access to on site parking. Within a few steps, you will arrive at the front door of the building. After entering and proceeding up one flight of stairs, you will find yourself at your home away from home. This private setting is nestled among single family homes. Once inside the unit, you will notice it has been professionally decorated with brand new furniture in a contemporary style for today's modern traveler.

Guest favourite

Rental unit in Milton

4.86 out of 5 average rating, 117 reviews

Retreat Milton/Boston line (transit close) Pets

The house is tastefully decorated and can accommodate a larger group , sleeps 6-8. 5 min to Boston , 1.3 miles to Central Ave Transit, or bus at end of street. The house is 20 min to Downtown Boston , it is a duplex totally separated for your own privacy. Reasonable alternative to Hotels , perfect for groups going to Convention Center. I recently added mini splits for additional cooling and heating needs , central ac .

Guest favourite

Rental unit in Randolph

4.87 out of 5 average rating, 323 reviews

1 Bedroom basement apartment

Apartment is in a basement of a one family house with a separate entrance and parking. Includes a private kitchen , bathroom and living room. located in Randolph Ma South of Boston,6 minutes to public transportation reachable only by car since you can only get there by taking the highway. We recommend our guests to rent a car or use uber. Closest train station is Quincy Adams Train Station, beaches , ski area

Guest favourite

Home in Dedham

4.98 out of 5 average rating, 220 reviews

Cozy, historic 3 bedroom home close to Boston!

Welcome to our cozy home. Our place blends historic charm with modern comfort. Enjoy a large, fenced yard with a grill, fire pit, and deck to relax. Inside, you'll find a well-equipped kitchen and a dining room. We offer three bedrooms with comfortable mattresses and soft bedding. The living room has a big TV with cable and streaming apps, plus high-speed Wi-Fi. Families with dogs are warmly welcomed.

Guest favourite

Rental unit in Milton

4.96 out of 5 average rating, 129 reviews

Milton - Immaculate & renovated 3 bed 2 .5 bath!

Welcome to our attached duplex family home. We recently renovated this home from top to bottom with brand new finishes and custom design. Our home has three large bedrooms with two full bathrooms with two living room areas that are a great fit for your family and friends. Some key features of the home are hardwood floors, quartz counter, bright recessed lights, and large yard for outdoor play.