Holiday rentals in Milton

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Top-rated holiday rentals in Milton

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

Guest favourite

Guest suite in Boston

4.96 out of 5 average rating, 201 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.

13–20 Dec

$173 SGD per night
Superhost

Flat in Boston

4.89 out of 5 average rating, 247 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.

15–22 Nov

$172 SGD per night
Guest favourite

Flat in Boston

4.92 out of 5 average rating, 214 reviews

Swanky unit nr. Everything/Restaurants/T/Downtown

My Swanky pad is a modern renovated garden level unit with a great open layout. Is very clean, comfortable, has private entrance, high ceilings, large windows which project great natural light into the space. Consist of: -- Kitchen w. Dining Space (work space) --Stainless steel appliances, full stove, refrigerator & over the range microwave --Keurig Coffee ( Complimentary coffee ), Electric hot water kettle --Large closets --55" Smart Tv in living room --High Speed WIFI --Full Bath with Tub

6–13 Apr

$156 SGD per night

Popular amenities for Milton holiday rentals

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 holiday rentals in Milton

Guest favourite

Home in Dedham

4.98 out of 5 average rating, 182 reviews

Cozy, historic 3 bedroom home close to Boston!

28 Sep – 5 Oct

$482 SGD per night
Guest favourite

Loft in Abington

4.99 out of 5 average rating, 116 reviews

Modern, Naturally lit Loft

10–17 Sep

$177 SGD per night
Superhost

Home in Boston

4.84 out of 5 average rating, 257 reviews

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

17–24 Nov

$207 SGD per night
Guest favourite

Guest suite in Brookline

4.88 out of 5 average rating, 178 reviews

Brookline Home with a Garden

19–26 Jun

$198 SGD per night
Guest favourite

Guest house in Framingham

4.97 out of 5 average rating, 194 reviews

Private guest house on beautiful country road

13–20 Mar

$150 SGD per night
Guest favourite

Loft in Boston

4.93 out of 5 average rating, 196 reviews

Sunny Artist Loft In Historic Brownstone

24–31 Aug

$229 SGD per night
Guest favourite

Guest suite in Boston

4.96 out of 5 average rating, 600 reviews

Cozy studio apartment in Jamaica plain!

$155 SGD per night
Guest favourite

Home in Dedham

5.0 out of 5 average rating, 143 reviews

The Gatehouse, Cheerful 3 bedroom 3 bathroom house

10–17 Aug

$697 SGD per night
Guest favourite

Guest suite in Scituate

4.91 out of 5 average rating, 173 reviews

Private Scituate Getaway - walk to harbor

24 Apr – 1 May

$188 SGD per night
Guest favourite

Guest suite in Watertown

4.92 out of 5 average rating, 261 reviews

Private 1BR Pied-a-terre

5–12 Nov

$129 SGD per night
Guest favourite

Flat in Framingham

4.9 out of 5 average rating, 300 reviews

Apartment Floris

4–11 Dec

$115 SGD per night
Guest favourite

Guest suite in Newton

4.98 out of 5 average rating, 551 reviews

Spacious suite with private entrance, parking spot

17–24 Aug

$179 SGD per night

Quick stats about holiday rentals in Milton

Total rentals

130 properties

Rentals with dedicated workspaces

60 properties have a dedicated workspace

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

50 properties are a good fit for families

Total number of reviews

4K reviews

Nightly prices starting at

$40 SGD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Norfolk County
  5. Milton