Milton Holiday Rentals

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Our top choices for Milton holiday rentals

10.0 out of 10, Exceptional, (16)
"Nice place to stay and easy to get to lots of attractions. "
United States
Michael J.
The price is NZ$907
includes taxes & fees
5 Jan - 6 Jan 2026
10-Spacious 5BR apt with gym, games room in the attic
9.4 out of 10, Exceptional, (3)
"The location had plenty of space for our family. Clean, close to shops and restaurants. Central location. "
United States
Andrea S.
The price is NZ$670
includes taxes & fees
30 Dec - 31 Dec
8-Peaceful & Bright apt/3br right to Boston line
9.4 out of 10, Exceptional, (8)
"Over all we had a great stay and Jenny was great to communicate with."
United States
Lori M.
The price is NZ$907
includes taxes & fees
11 Jan - 12 Jan 2026
14/2-SPRING GETAWAY EARLY BIRD 10% Spacious 5-bedroom apartment in Milton
2.0 star property
The price is NZ$1,129
includes taxes & fees
11 Jan - 12 Jan 2026
172/2 - 6BR Milton - Family Getaway by Blue Hills
9.4 out of 10, Exceptional, (11)
"The apartment is very clean and the host is very responsive. "
United States
Ye R.
The price is NZ$621
includes taxes & fees
2 Jan - 3 Jan 2026
14/1 - SPRING GETAWAY EARLY BIRD 10%! 3-bedroom apartment in peaceful Milton

Houseboat in Thompson Square - Bunker Hill

Charlestown Houseboat Walk to attractions Be rocked to sleep
9.6 out of 10, Exceptional, (99)
"Great location, pet friendly, "
United States
Karen W.
The price is NZ$727
includes taxes & fees
5 Jan - 6 Jan 2026
Charlestown Houseboat Walk to attractions Be rocked to sleep
10.0 out of 10, Exceptional, (57)
"Amazing location, Boston is a favorite of ours. Go Sox"
United States
jeff w.
The price is NZ$617
includes taxes & fees
3 Jan - 4 Jan 2026
Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by
9.8 out of 10, Exceptional, (200)
"My husband and I had an excellent stay! It was very comfortable! I would highly recommend staying on The Blue Pearl and hope to stay there again. "
United States
Stacey W.
The price is NZ$798
includes taxes & fees
4 Jan - 5 Jan 2026
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Apartment in Downtown Boston

Temple Place Suites
2.5 star property
7.0 out of 10, Good, (328)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is NZ$286
includes taxes & fees
30 Dec - 31 Dec
Temple Place Suites
4.0 star property
8.0 out of 10, Very good, (637)
"Very clean, beautiful place. I would stay there again."
Canada
Liam
Global Luxury Suites Downtown Boston
2.0 star property
7.2 out of 10, Good, (134)
"Good location, compact room with everything you need. Very convenient self-service token-operated washing machine and dryer. Worth the price. No elevators, and bed is a bit small."
United Kingdom
Fanny Pei Yee
Maverick Suites at 400 Columbus Ave

Aparthotel in Beacon Hill

Maverick Suites at 40 Temple St
2.0 star property
7.6 out of 10, Good, (102)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
Maverick Suites at 40 Temple St

Aparthotel in Bay Village

Bay Village Suites
2.0 star property
6.6 out of 10, (252)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites

Aparthotel in Back Bay

Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very good, (155)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
Maverick Suites at 245 Newbury St

Aparthotel in Bay Village

Premier Suites - Bay Village
2.0 star property
6.4 out of 10, (252)
"Clean room, good location, check in check out easily!"
United States
HIEN T
Premier Suites - Bay Village
2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice room. Good location "
United States
Abenamar A.
The price is NZ$588
includes taxes & fees
1 Jan - 2 Jan 2026
The Chester: Hip, Renovated, South End

Apartment in Fenway–Kenmore

Maverick Suites at 28 Fenway
3.0 star property
8.6 out of 10, Excellent, (330)
"Good place"
United States
Elijah
The price is NZ$354
includes taxes & fees
5 Jan - 6 Jan 2026
Maverick Suites at 28 Fenway

Apartment in Downtown Boston

Best Location Studio In Downtown Boston
10.0 out of 10, Exceptional, (1)
"In town to celebrate a special event."
United States
Pam P.
The price is NZ$386
includes taxes & fees
6 Jan - 7 Jan 2026
Best Location Studio In Downtown Boston

Aparthotel in South End

The Chester Hotel
4.0 star property
8.6 out of 10, Excellent, (28)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
The price is NZ$600
includes taxes & fees
1 Jan - 2 Jan 2026
The Chester Hotel
10.0 out of 10, Exceptional, (3)
"This place is so cool! Was incredibly clean, updated and offered all the amenities you need for a weekend get away. The location is wonderful as well with lots of markets, bakeries and restaurants all within walking distance. This is a must stay! "
United States
mary j.
The price is NZ$972
includes taxes & fees
30 Dec - 31 Dec
3BR3Bth Entire House/Steps to Downtown & TD Garden
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Milton Hotel Reviews

Find out more about Milton

Everything you need to know about Milton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Milton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Milton holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Milton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Milton. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Milton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Milton holiday rentals we have selected for you start as low as NZ$286 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Milton rentals

At Expedia, we put the best Milton holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Milton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Milton holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Milton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Milton?

Yes, there are holiday rentals in Milton close to Blue Hills Reservation, or you can select a more secluded option if you're looking for a relaxing stay. Milton is known for its shopping and restaurants.

What are some of the best holiday rentals that Milton has to offer?

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi: This holiday home rental outside of Milton is located in the city centre, and offers a balcony, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Milton?

With 10 Expedia holiday rentals, you're guaranteed to find just the right place for your Milton stay.

What can I see and do in Milton?

Family-friendly attractions include Blue Hills Reservation and Pierce Reservation, whereas Governor Hutchinson's Field is a spot to enjoy the outdoors. Other popular places to visit in the area include Fenway Park and TD Garden.

What are holiday rentals like in Milton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Milton. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for families.