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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

4.92 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 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 suite in Jamaica Central - South Sumner

4.92 out of 5 average rating, 215 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.

Guesthouse in Scituate

4.92 out of 5 average rating, 103 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!

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 suite in Dover

4.97 out of 5 average rating, 235 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

4.93 out of 5 average rating, 141 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

4.8 out of 5 average rating, 219 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!

Rental unit in Quincy

4.87 out of 5 average rating, 352 reviews

Easy Train/Boston -Two Bedroom North Quincy

Gorgeous place. All brand new, high-end. You’ll love the sleek design, brand new central AC, Open kitchen, Cool Breakfast Bar, luxury bathroom and tempurpedic mattresses! FREE PARKING (2 spots-tandem-right next to entrance to unit!) Fantastic location: walk to several great restaurants, bars, shops and 3 minute walk to train to downtown Boston (4 stops on train-about 25 minutes) & The Seaport District. Wollaston Beach 1/2 mile away.

Rental unit in Milton

4.86 out of 5 average rating, 118 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

4.87 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

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.

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

4.96 out of 5 average rating, 49 reviews

Milton Retreat: 10 Min to Boston, Near Amenities

Rental unit in Quincy

4.86 out of 5 average rating, 78 reviews

Cozy KING BED Suite in Greater Boston Area

Guest suite in Braintree

4.82 out of 5 average rating, 79 reviews

Lakeside studio apt @ Sunset Lake. Kayaks for use!

Home in Greater Mattapan

5 out of 5 average rating, 26 reviews

The Enchanted Red Doors

Rental unit in Greater Mattapan

4.82 out of 5 average rating, 60 reviews

Modern 1 BR Apt w| Full Kitchen & Private Driveway

Home in Milton

4.99 out of 5 average rating, 67 reviews

Spacious, Comfy Colonial min. to Boston

Rental unit in Milton

5 out of 5 average rating, 5 reviews

14/1 - Warm & cozy 3BR apatment in Milton

Rental unit in Newton

4.92 out of 5 average rating, 313 reviews

Conveniently Located Private Garden Apartment

Quick stats about vacation rentals in Milton

Total rentals
130 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
4.5K 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 280 vacation rentals in West Street - River Street, over 280 vacation rentals in Hyde Park, and over 2,580 vacation rentals in Montclair.
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 House Rentals in Milton?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with wifi, over 50 homes with air conditioning, over 40 homes with free parking, over 40 homes with a kitchen, 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.

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