Vacation rentals in Milton

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Top-rated vacation rentals in Milton

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Guest favorite

Guest suite in Boston

4.96 out of 5 average rating, 202 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.

Mar 5 – 12

$111 per night

Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 102 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

Mar 12 – 19

$88 per night

Superhost

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.

Mar 11 – 18

$111 per night

Guest favorite

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 2 – 9

$94 per night

Guest favorite

Guest suite in Sharon

4.97 out of 5 average rating, 143 reviews

Cozy Lakeview Guesthouse

This Lakeview Guesthouse is private and stunning! It has its private entrance, deck, and parking. It features 1 bedroom with a Queen Bed, TV, with a sliding door that opens to a deck. The living room has a view of the Lake and a smart TV. The bathroom includes a tub (not a jacuzzi) and sitting on bench shower. The kitchen is fully equipped with stainless steel appliances. Guests have access to the lake, via beach pass during the summer. During the winter you can skate at your own risk.

Jan 11 – 18

$149 per night

Guest favorite

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 5 – 12

$130 per night

Guest favorite

Home in Boston

4.91 out of 5 average rating, 296 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

Feb 11 – 18

$122 per night

Guest favorite

Guest suite in Abington

4.87 out of 5 average rating, 291 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

Jan 22 – 29

$141 per night

Guest favorite

Apartment in Milton

4.85 out of 5 average rating, 106 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 .

Sep 19 – 26

$408 per night

Guest favorite

Cottage in Milton

4.95 out of 5 average rating, 170 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.

Nov 3 – 10

$225 per night

Guest favorite

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

Oct 1 – 8

$115 per night

Guest favorite

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 22 – 29

$100 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Milton vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Milton's top sights

Massachusetts State House118 locals recommend

AMC Braintree 1022 locals recommend

MATTAPAN SQUARE3 locals recommend

FLAMING GRILL & BUFFET (Roslindale Location)5 locals recommend

Star Market81 locals recommend

Shaw's12 locals recommend

Other great vacation rentals in Milton

Guest favorite

Guest suite in Brookline

4.87 out of 5 average rating, 183 reviews

Brookline Home with a Garden

Aug 12 – 19

$128 per night

Guest favorite

Guest suite in Norwell

4.95 out of 5 average rating, 260 reviews

Private suite South Shore

Sep 28 – Oct 5

$107 per night

Superhost

Apartment in Weymouth

4.81 out of 5 average rating, 162 reviews

Lovely studio on the coast! Beach close by!

Jul 26 – Aug 2

$153 per night

Superhost

Apartment in Avon

4.85 out of 5 average rating, 110 reviews

Welcoming and Sunny

Nov 28 – Dec 5

$91 per night

Guest favorite

Loft in Abington

4.99 out of 5 average rating, 119 reviews

Modern, Naturally lit Loft

Jan 7 – 14

$108 per night

Superhost

Home in Canton

4.84 out of 5 average rating, 144 reviews

3 bedroom impeccable private home, quiet street

Dec 28 – Jan 4

$149 per night

Guest favorite

Guest suite in Boston

4.93 out of 5 average rating, 285 reviews

Washer+Dryer+Parking!*Private suite*Cul de sac*

Jun 19 – 26

$111 per night

Superhost

Guest suite in Braintree

4.79 out of 5 average rating, 53 reviews

Lakeside apartment entire studio. Kayaks for use!

Sep 12 – 19

$120 per night

Show all

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
$30 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 West Street - River Street, over 260 vacation rentals in Hyde Park, 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 house rentals in Milton have wifi?
Absolutely! We offer over 60 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 60 homes with wifi, over 50 homes with a kitchen, over 40 homes with free parking, over 50 homes with air conditioning, 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 house rentals in Milton have a kitchen?
Absolutely! We offer over 50 house 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.

Vacation rentals in Milton

Top-rated vacation rentals in Milton

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Milton vacation rentals

Stay near Milton's top sights

Other great vacation rentals in Milton

Guest suite in Brookline

Guest suite in Norwell

Apartment in Weymouth

Apartment in Avon

Loft in Abington

Home in Canton

Guest suite in Boston

Guest suite in Braintree

Quick stats about vacation rentals in Milton

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Milton?

Do house rentals in Milton have free parking?

Where should I stay in Milton?

Are there family-friendly vacation rentals in Milton?

Do house rentals in Milton have wifi?

Are there pet-friendly vacation rentals in Milton?

What are the most popular amenities for House Rentals in Milton?

How much does it cost to stay in house rentals in Milton?

Do house rentals in Milton have a kitchen?

Do apartment rentals in Milton have air conditioning?

Destinations to explore