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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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Apartment in Boston

4.89 out of 5 average rating, 251 reviews

🎖The Boiler Room | Close to Subway + Downtown🎖

This unique private suite is brand new & comes w/ its own private entrance. Including a queen size bed, ensuite bathroom, & a wine/craft beer minibar! The unit is extremely clean and very nicely decorated. A quick 5 minute walk to Ashmont Station (Red Line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. Great restaurants nearby - Molinari's & Tavolo Ristorante - as well as a local coffee shop + a Dunkin just across the Ashmont metro station.

Jan 4 – 11

R2,295 ZAR per night

Guest suite in Boston

4.96 out of 5 average rating, 203 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.

Apr 8 – 15

R2,451 ZAR per night

Loft in Abington

4.99 out of 5 average rating, 119 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!

Apr 9 – 16

R2,464 ZAR per night

Guest suite in Winchester

5.0 out of 5 average rating, 104 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

Dec 29 – Jan 5

R2,260 ZAR per night

Guest suite in Boston

4.91 out of 5 average rating, 196 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.

Oct 13 – 20

R2,058 ZAR per night

Guest suite in Watertown

4.91 out of 5 average rating, 264 reviews

Private 1BR Pied-a-terre

Fully furnished mini-suite with private entrance; walk in at ground level. Picture window view of, and use of, large back yard. Separate sitting and sleeping areas (full size bed), desk/workspace, bathroom with shower, kitchenette with small fridge, coffeemaker and microwave (no stove). Great take-out nearby. No pets, no smoking permitted. Car? There is off-street covered parkling. No car? 71 Bus to Harvard Square stops at our corner; short walk to other buses and public transportation.

Dec 5 – 12

R1,822 ZAR per night

Guest suite in Dover

4.98 out of 5 average rating, 182 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.

Mar 11 – 18

R2,852 ZAR per night

Home in Boston

4.84 out of 5 average rating, 261 reviews

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

Relax in the Bostonian, a stylish, pet-friendly apartment on the semi-basement level of a charming multi-family house. The apartment is air conditioned and overlooks a beautiful patio and backyard. Located in quiet Hyde Park neighborhood, a 30 minute drive into downtown Boston. Plenty of free streetside parking. In unit laundry. Professionally cleaned and disinfected. Room 1: Queen size bed, closet Room 2: Queen size bed, dresser Room 3: Living room couch, TV, electric fireplace

Jan 17 – 24

R2,458 ZAR per night

Apartment in Weymouth

4.8 out of 5 average rating, 164 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!

Sep 6 – 13

R2,348 ZAR per night

Cottage in Milton

4.95 out of 5 average rating, 171 reviews

Walk to it all-shops, market, dinner, coffee shops

Nestled in a quiet neighborhood, this enchanting cottage embodies the essence of coziness and charm, adorned with a delightful mid-century flair. Offering an idyllic sanctuary of seclusion, it has been thoughtfully crafted to become your cherished haven away from the hustle and bustle of everyday life. The number of people allowed to stay is 3 unless you are a family with younger children and then 4 people with be fine.

Mar 5 – 12

R4,913 ZAR per night

Apartment in Randolph

4.88 out of 5 average rating, 283 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

Dec 30 – Jan 6

R2,508 ZAR per night

Home in Quincy

4.96 out of 5 average rating, 123 reviews

Artist's Haven (2)

Before booking, please conduct thorough research on Quincy, MA, to ensure it aligns perfectly with your needs. As a dedicated Superhost, I'm committed to earning your 5-star review. My home offers easy check-in with a keypad entry. The cozy second-floor one-bedroom has a private entrance, spa-like bathroom, well-equipped kitchen, queen-sized bed, 55" TV, high-speed WiFi, and on-site parking for one car.

Jun 20 – 27

R2,210 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

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Convenient locations with everyday essentials

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Stylish accommodations and amenities

Popular amenities for Milton vacation rentals

Free parking on premises

Air conditioning

Stay near Milton's top sights

Massachusetts State House118 locals recommend

MATTAPAN SQUARE3 locals recommend

AMC Braintree 1022 locals recommend

FLAMING GRILL & BUFFET (Roslindale Location)5 locals recommend

Star Market81 locals recommend

Shaw's12 locals recommend

Other great vacation rentals in Milton

Apartment in Milton

4.85 out of 5 average rating, 106 reviews

Retreat Milton/Boston line (transit close) Pets

Sep 18 – 25

R8,946 ZAR per night

Guest suite in Stoughton

4.99 out of 5 average rating, 160 reviews

Modern private studio with outdoor hot tub!

Aug 11 – 18

R5,450 ZAR per night

Guest suite in Abington

4.87 out of 5 average rating, 292 reviews

South Shore Luxury Apartment

Aug 23 – 30

R3,103 ZAR per night

Home in Boston

4.89 out of 5 average rating, 295 reviews

Treetop Haven in the City

Dec 28 – Jan 4

R2,385 ZAR per night

Apartment in Natick

4.98 out of 5 average rating, 332 reviews

Scandi-Modern Apartment

Sep 27 – Oct 4

R2,425 ZAR per night

Apartment in Boston

4.88 out of 5 average rating, 491 reviews

Serene Studio in a Perfect Location

Oct 10 – 17

R2,997 ZAR per night

Home in Dedham

4.98 out of 5 average rating, 182 reviews

Cozy, historic 3 bedroom home close to Boston!

Nov 20 – 27

R6,532 ZAR per night

Guest suite in Newton

4.97 out of 5 average rating, 556 reviews

Spacious suite with private entrance, parking spot

Aug 12 – 19

R2,667 ZAR per night

Quick stats about vacation rentals in Milton

Total rentals
130 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
4K reviews
Nightly prices starting at
R573 ZAR before taxes and fees

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 house rentals in Milton have free parking?
Absolutely! We offer over 40 house 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 260 vacation rentals in Hyde Park, over 260 vacation rentals in West Street - River Street, and over 2,540 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 apartment rentals in Milton have wifi?
Absolutely! We offer over 40 apartment 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 wifi, over 40 homes with a kitchen, over 40 homes with air conditioning, over 30 homes with free parking, 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 apartment rentals in Milton have air conditioning?
Absolutely! We offer over 40 apartment rentals with air conditioning in Milton. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore