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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Milton holiday rentals

A modern living room with a grey sofa, a white coffee table, and a bookshelf with decorative items.

1. 10-Spacious 5BR apt with gym, games room in the attic

10-Spacious 5BR apt with gym, games room in the attic
Milton
9.8 out of 10, Exceptional, (23 reviews)
"Nice place to stay and easy to get to lots of attractions. "
United States
Michael J.
The price is £346
includes taxes & fees
10 Nov - 11 Nov
10-Spacious 5BR apt with gym, games room in the attic
A modern kitchen with white cabinets, a refrigerator, and a dining area with a table and chairs.

2. 14/2-SPRING GETAWAY EARLY BIRD 10% Spacious 5-bedroom apartment in Milton

14/2-SPRING GETAWAY EARLY BIRD 10% Spacious 5-bedroom apartment in Milton
Milton
9.6 out of 10, Exceptional, (12 reviews)
"The house was clean and pet friendly. Had enough rooms for everyone."
United States
Monica
The price is £285
includes taxes & fees
10 Nov - 11 Nov
14/2-SPRING GETAWAY EARLY BIRD 10% Spacious 5-bedroom apartment in Milton
A white door with frosted glass panels, a small plant on a wooden stand, and a white textured vase on a white surface.

3. 8-Peaceful & Bright apt/3br right to Boston line

8-Peaceful & Bright apt/3br right to Boston line
Milton
9.8 out of 10, Exceptional, (6 reviews)
"Excellent in all respects "
United States
bob p.
The price is £271
includes taxes & fees
10 Nov - 11 Nov
8-Peaceful & Bright apt/3br right to Boston line
A two-story house with a stone staircase leading to the front door, surrounded by well-maintained bushes and a brick pathway.

4. Prestigious Milton Designer Home

Prestigious Milton Designer Home
Milton
10.0 out of 10, Exceptional, (4 reviews)
"Great house!! So clean- great space! Close to the city- but far enough away as well. . We had a great time!"
United States
Kellie R.
The price is £442
includes taxes & fees
1 Dec - 2 Dec
Prestigious Milton Designer Home
A hallway leading to a dining area with wooden flooring and white walls.

5. 14/1 - SPRING GETAWAY EARLY BIRD 10%! 3-bedroom apartment in peaceful Milton

14/1 - SPRING GETAWAY EARLY BIRD 10%! 3-bedroom apartment in peaceful Milton
Milton
9.4 out of 10, Exceptional, (21 reviews)
"Enjoyed our stay."
United States
Deborah M.
The price is £213
includes taxes & fees
12 Nov - 13 Nov
14/1 - SPRING GETAWAY EARLY BIRD 10%! 3-bedroom apartment in peaceful Milton
A modern kitchen with white cabinetry, a central island with bar stools, stainless steel appliances, and pendant lighting.

6. Peaceful Milton Getaway- Trails & City Nearby

Peaceful Milton Getaway- Trails & City Nearby
Milton
10.0 out of 10, Exceptional, (3 reviews)
"Very beautiful place and clean. The hosts were very nice and gave speedy responses. "
United States
The P.
The price is £806
includes taxes & fees
7 Dec - 8 Dec
Peaceful Milton Getaway- Trails & City Nearby
A modern living room with a sofa set, a coffee table, and a potted plant.

7. Spacious 6BR Family Stay Near Boston/Blue Hills, Free Parking & Pet-Friendly 172

Spacious 6BR Family Stay Near Boston/Blue Hills, Free Parking & Pet-Friendly 172
Milton
6.0 out of 10, (1 review)
The price is £343
includes taxes & fees
10 Nov - 11 Nov
Spacious 6BR Family Stay Near Boston/Blue Hills, Free Parking & Pet-Friendly 172
A bunk bed room with a window, a lamp, a small table, and a Mickey Mouse plush toy.

8. Spacious 5BR Executive Retreat - 10 Min to Boston

Spacious 5BR Executive Retreat - 10 Min to Boston
Milton
The price is £587
includes taxes & fees
7 Dec - 8 Dec
Spacious 5BR Executive Retreat - 10 Min to Boston
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

9. New Built & Modern 3BR Boston w/ Parking, Pet Friendly near Franklin Park 602

New Built & Modern 3BR Boston w/ Parking, Pet Friendly near Franklin Park 602
Mattapan
9.4 out of 10, Exceptional, (30 reviews)
"Our stay was wonderful. The house was exactly what was pictured. Very clean and brand new. Felt very comfortable. Nicely decorated. Beds were very comfortable as well. Linens and towels were provided as well as shampoo and body wash and hair dryer. Bedrooms are large as well. Great for large groups too. Our host was very nice and easy to contact. She also replied right away. You always hear about the owner not responding right away, but Jenny always did. I highly recommend!"
United States
Julia
The price is £260
includes taxes & fees
10 Nov - 11 Nov
New Built & Modern 3BR Boston w/ Parking, Pet Friendly near Franklin Park 602
A modern kitchen with white cabinetry, stainless steel appliances, a large island with bar stools, pendant lighting, and a view of the outdoors through a window.

10. 🎖The Ashmont Suite - Close to Subway + Downtown🎖

🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dorchester
10.0 out of 10, Exceptional, (62 reviews)
"We had a great visit and the house gave us everything we needed for a comfortable stay. The rooms were nicely furnished and the bedrooms were spacious. The location was convenient for accessing the bus and the subway. The host was very friendly and responsive. We hope to visit again!"
United States
Christina B.
The price is £409
includes taxes & fees
23 Nov - 24 Nov
🎖The Ashmont Suite - Close to Subway + Downtown🎖
A wooden front door with a glass panel and the number 383.

11. Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383
Quincy
9.8 out of 10, Exceptional, (53 reviews)
"Extraordinarily beautiful VRBO, very clean, convenient to highway, walking distance to several eateries, walk or quick drive to the Red Line to use to get into downtown Boston, and very responsive owner."
United States
Mark T.
The price is £243
includes taxes & fees
10 Nov - 11 Nov
Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383
A kitchen with white cabinets, a tiled backsplash, and a knife block on the counter.

12. Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39
Quincy
9.6 out of 10, Exceptional, (57 reviews)
"Very clean and stay was enjoyable. "
United States
Sheldon S.
The price is £243
includes taxes & fees
10 Nov - 11 Nov
Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

13. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (44 reviews)
"I had a great stay at The Chester Hotel. Super cute vibe, easy check-in, and good location for where I needed to be for work. Bed is super comfy, the room aesthetic is great and the restaurant MIDA next door was really good!"
United States
Tracy
The price is £219
includes taxes & fees
10 Nov - 11 Nov
The Chester Hotel
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

14. Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams

Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams
Quincy
9.8 out of 10, Exceptional, (9 reviews)
"Perfect stay for the night. Communication was great and property was clean and had everything we needed."
United States
Ryan E.
The price is £239
includes taxes & fees
16 Nov - 17 Nov
Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams
A neatly arranged bedroom with a bed, bedside tables, a dresser, and a window providing natural light.

15. Cozy three-bedroom home close to Boston w/ plenty of parking

Cozy three-bedroom home close to Boston w/ plenty of parking
North Braintree
10.0 out of 10, Exceptional, (60 reviews)
"Great overall stay!"
United States
Chris R.
The price is £326
includes taxes & fees
10 Nov - 11 Nov
Cozy three-bedroom home close to Boston w/ plenty of parking
A view of a beach with cars parked on the side of the road, a pedestrian crossing, and a wooden fence.

16. Renovated Beach House Close to Everything, Minutes to Boston

Renovated Beach House Close to Everything, Minutes to Boston
Quincy
9.2 out of 10, Wonderful, (126 reviews)
"Great location! Owner was responsive with any issues."
United States
Samuel K.
The price is £296
includes taxes & fees
10 Nov - 11 Nov
Renovated Beach House Close to Everything, Minutes to Boston
A kitchen with white cabinets, a tiled backsplash, and a knife block on the counter.

17. Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41
Quincy
9.6 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay at this place. Comfortable and plenty of space for us."
United States
Jeff L.
The price is £280
includes taxes & fees
19 Nov - 20 Nov
Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

18. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (350 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is £222
includes taxes & fees
24 Nov - 25 Nov
Kasa Boston at Fenway
An outdoor patio area with a covered seating area, a fire pit, and a well-lit ambiance.

19. 🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖

🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Dorchester
9.8 out of 10, Exceptional, (126 reviews)
"Host was very friendly and attentive, responded quickly to messages. Everything worked out as planned and we’d love to stay there again the next time we come to Boston! Thanks for a great place to stay."
United States
Michael P.
The price is £294
includes taxes & fees
15 Nov - 16 Nov
🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

20. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,352 reviews)
"Wehave stayed here several times and each time has been a pleasure."
United States
Kasandra
The price is £120
includes taxes & fees
12 Nov - 13 Nov
Crescent Suites Hotel
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

An outdoor seating area with a fire pit, sofas, and chairs.
Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District
Seaport District

10/10 Excellent

A really comfortable room in a good location, particularly useful for accessing the airport as the Silver Line Way bus stop is literally around the corner. Service was excellent and really helpful to us considering the times we arrived and wanted to get to the airport for. Breakfast was good too.
United Kingdom
Karl
Reviewed November 2, 2024
Hyatt Place Boston/Seaport District

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, apart-hotels, 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 £152 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?

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This holiday home rental outside of Milton offers a patio, a garden and air conditioning 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. Kick off your shoes and enjoy yourself with 1 hot tub and a selection of books.

How many holiday rentals are there in Milton?

With 15 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 Gillette Stadium.

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.