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Vacation rentals in Milton

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Top-rated vacation rentals in Milton

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

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Guest suite in Dorchester

4.9 out of 5 average rating, 102 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 suite in Dorchester

4.96 out of 5 average rating, 220 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.

Loft in Abington

4.99 out of 5 average rating, 133 reviews

Modern, Naturally lit Loft

Enjoy a quiet getaway, with private entrance, in a private loft apartment situated in South Shore, MA. The loft is a large, open floorplan flooded with natural light. Enjoy nature walks at the Abington/Hanover rail trail for a great morning walk or a nice evening on the private balcony. There is a full-size kitchen in the loft at your disposal. We have a parking space in front of the house, fast WIFI, and a designated desk for work if you need it. This loft Is amazingly comfortable and peaceful!

Guest suite in Jamaica Central - South Sumner

4.91 out of 5 average rating, 209 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.

Home in Hyde Park

4.91 out of 5 average rating, 314 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

Home in Quincy

4.96 out of 5 average rating, 139 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 suite in Dover

4.97 out of 5 average rating, 220 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 suite in Roslindale

4.95 out of 5 average rating, 131 reviews

Cozy Renovated Suite w/Free St Parking near Train

Newly renovated in-law suite located in the charming Roslindale neighborhood of Boston. A short walk from West Roxbury Center, Roslindale Village's shops and restaurants, and Bellevue commuter rail stop which gets you to Back Bay in 15 mins (or 20 Min Uber/drive). Features include a private entrance kitchenette, bathroom, large quiet back yard with patio and fire pit (avail Apr-Oct). Perfect for weekend getaways, working/commuting to Boston, or visiting friends and family!

Guest suite in Weymouth

4.81 out of 5 average rating, 202 reviews

Lovely studio on the coast! Beach close by!

Wonderful location located in north Weymouth. Quiet, Spacious studio apartment. Outdoor deck with patio furniture. Plenty of space for 3 guests max. - Walking distance to George lane beach & Wessagusset beach. - Convenience store, Pizza & Sandwich shop on our block. - 2 miles to Hingham shipyard - 5 miles to Nantasket beach - In between several commuter rail stations and across the street from a bus stop. - 4 miles to Quincy center - 30 minute drive to Boston!

Guest suite in Abington

4.88 out of 5 average rating, 311 reviews

South Shore Luxury Apartment

Luxury in-law suite with new appliances, new bed and bedroom furniture, heated bathroom floors, jacuzzi tub, electric fireplace, and off street parking just steps from your own private entrance nestled into the Ames Nowell State Park. Just minutes away from the South Shore Hospital, make this your home away from home! FireTV, Echo Studio, Wii console & games in living room for guest use. 2 hours Early Check-in/Late Check-out available $30

Rental unit in Milton

4.86 out of 5 average rating, 116 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 .

Rental unit in Randolph

4.88 out of 5 average rating, 312 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

Vacation rentals for every style

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Popular amenities for Milton vacation rentals

Free parking on premises

Air conditioning

Stay near Milton's top sights

Star Market81 locals recommend

Ashmont Grill56 locals recommend

South Shore Plaza55 locals recommend

Sophia's Grotto52 locals recommend

CVS49 locals recommend

Fornax Bread Company38 locals recommend

Other great vacation rentals in Milton

Rental unit in Milton

4.94 out of 5 average rating, 34 reviews

Milton Retreat: 10 Min to Boston, Near Amenities

Rental unit in Quincy

4.93 out of 5 average rating, 149 reviews

Sunny, clean Wollaston 2BR near Red Line and beach

Home in Canton

4.82 out of 5 average rating, 159 reviews

3 bedroom impeccable private home, quiet street

Guest suite in Concord

4.97 out of 5 average rating, 107 reviews

Water front cabin-like guest suite on a quiet pond

Rental unit in Quincy

4.84 out of 5 average rating, 62 reviews

Cozy KING BED Suite in Greater Boston Area

Guesthouse in Dorchester

4.86 out of 5 average rating, 88 reviews

Prime City Location: Private Suite-separate entry.

Guest suite in Winchester

5 out of 5 average rating, 151 reviews

Warm and cozy 1st flr sweet guest suite w parking

Loft in Brockton

4.97 out of 5 average rating, 37 reviews

Modern Studio Apt with Pool

Quick stats about vacation rentals in Milton

Total rentals
130 properties
Nightly prices starting at
G$6,262 GYD before taxes and fees
Total number of reviews
4.1K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Milton?
Yes! Work meets play with ease at over 70 vacation rentals in Milton featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Milton have free parking?
Absolutely! We offer over 30 apartment rentals with free parking in Milton. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Milton?
Make yourself at home in Milton by choosing from our most frequently booked neighborhoods. We have over 2,650 vacation rentals in Montclair, over 270 vacation rentals in Hyde Park, and over 270 vacation rentals in West Street - River Street.
Are there family-friendly vacation rentals in Milton?
Milton has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Milton have wifi?
Absolutely! We offer over 50 house rentals with wifi in Milton. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Milton?
Four-legged friends are welcome in Milton. Choose from more than 30 vacation rentals for guests traveling with pets.
What are the most popular amenities for Apartment Rentals in Milton?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with a kitchen, over 30 homes with free parking, over 40 homes with air conditioning, over 50 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Milton?
Experience the best of Milton with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Milton have a kitchen?
Absolutely! We offer over 40 apartment rentals with a kitchen in Milton. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Milton have air conditioning?
Absolutely! We offer over 50 house rentals with air conditioning in Milton. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore