A forest path with tall trees and sunlight filtering through.

Milton Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Milton vacation rentals

A hallway leading to a dining area with wooden flooring and white walls.

1. FREE Parking & Bright 3BR Boston Stay 1st-floor Apt • Pet-Friendly Near I-93 141

FREE Parking & Bright 3BR Boston Stay 1st-floor Apt • Pet-Friendly Near I-93 141
Milton
9.2 out of 10, Wonderful, (19 reviews)
"Enjoyed our stay."
United States
Deborah M.
$402 nightly
The price is $425
Nov 1 - Nov 2
Total with taxes and fees
FREE Parking & Bright 3BR Boston Stay 1st-floor Apt • Pet-Friendly Near I-93 141
A two-story house with a stone staircase leading to the front door, surrounded by well-maintained bushes and a brick pathway.

2. Prestigious Milton Designer Home

Prestigious Milton Designer Home
Milton
10.0 out of 10, Exceptional, (2 reviews)
"From initial contact with Serene the communication could not have been any better. The house is wonderful and ideally located to all amenities in Milton. The bedrooms and living areas comfortable. Big shout out to the people of Milton! We were treated like minor celebrities. Applauded into Chans Chinese restaurant..free beers...and everyone so warm and welcoming. If Scotland get back to Boston and you are a larger group (we were 8) then book it!"
United States
Marl R.
$520 nightly
The price is $549
Oct 6 - Oct 7
Total with taxes and fees
Prestigious Milton Designer Home
A modern living room with a grey sofa, a white coffee table, and a bookshelf with decorative items.

3. 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)
"Perfect fit for our group!"
United States
Nancy L.
$565 nightly
The price is $597
Oct 12 - Oct 13
Total with taxes and fees
10-Spacious 5BR apt with gym, games room in the attic
A white door with frosted glass panels, a small plant on a wooden stand, and a white textured vase on a white surface.

4. 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.
$472 nightly
The price is $499
Oct 11 - Oct 12
Total with taxes and fees
8-Peaceful & Bright apt/3br right to Boston line
A modern living room with a sofa set, a coffee table, and a potted plant.

5. 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)
$548 nightly
The price is $579
Oct 12 - Oct 13
Total with taxes and fees
Spacious 6BR Family Stay Near Boston/Blue Hills, Free Parking & Pet-Friendly 172
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.
$1,318 nightly
The price is $1,411
Nov 2 - Nov 3
Total with taxes and fees
Peaceful Milton Getaway- Trails & City Nearby
A modern kitchen with dark cabinets, a large island, and pendant lighting.

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

Spacious 5BR Executive Retreat - 10 Min to Boston
Milton
$722 nightly
The price is $763
Oct 28 - Oct 29
Total with taxes and fees
Spacious 5BR Executive Retreat - 10 Min to Boston
A modern kitchen with white cabinets, a refrigerator, and a dining area with a table and chairs.

8. Cozy 5BR Milton Home • Pet-Friendly near I-93 & Blue Hills 14-2

Cozy 5BR Milton Home • Pet-Friendly near I-93 & Blue Hills 14-2
Milton
9.4 out of 10, Exceptional, (10 reviews)
"The space was perfect for a family of 12 traveling together. Our host was very responsive and made sure we had everything we needed for the stay. We highly recommend it should you need a lot of rooms in a nice quiet neighborhood. We would definitely stay there again should the need arise. "
United States
Anonymous traveler
$417 nightly
The price is $441
Oct 6 - Oct 7
Total with taxes and fees
Cozy 5BR Milton Home • Pet-Friendly near I-93 & Blue Hills 14-2
A room with a large window overlooking a marina with boats and buildings.

9. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (115 reviews)
"Rustic boathouse in a great central location ."
United States
William M.
$453 nightly
The price is $521
Nov 4 - Nov 5
Total with taxes and fees
Fun houseboat. Walk to Boston attractions WIFI
A marina with boats docked, a red brick building, and modern high-rise apartments in the background.

10. Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Charlestown
9.8 out of 10, Exceptional, (210 reviews)
"Such a quaint and quiet location. We loved staying on the pier. The boat was clean and tidy!! We would definitely stay there again!!"
United States
Angela L.
$470 nightly
The price is $540
Nov 3 - Nov 4
Total with taxes and fees
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
A waterfront building with a sign reading "Turtle," featuring a dock with red chairs and potted plants.

11. Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC

Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
Thompson Square - Bunker Hill
9.8 out of 10, Exceptional, (75 reviews)
"Great location and the host was very helpful for everything. Definitely I’m gonna stay here again."
United States
Sandy M.
$419 nightly
The price is $482
Oct 7 - Oct 8
Total with taxes and fees
Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
An outdoor patio area with a covered seating area, a fire pit, and a well-lit ambiance.

12. 🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (94 reviews)
"Honestly, the Boiler Room is even bigger than it looks in the pictures and is so perfectly curated! We LOVED our stay and if I ever get the opportunity to come back to Boaton, I will be staying here!"
United States
Katie C.
$283 nightly
The price is $325
Oct 18 - Oct 19
Total with taxes and fees
🎖The Boiler Room - Close to Subway & Downtown🎖
A modern kitchen with a large island, white cabinets, and pendant lighting.

13. Family-Friendly 3BR Apt - Easy Downtown Boston Accesss - near Franklin Park 603

Family-Friendly 3BR Apt - Easy Downtown Boston Accesss - near Franklin Park 603
Mattapan
9.6 out of 10, Exceptional, (29 reviews)
"Perfect home. Great location. Would recommend!!!!"
United States
Nicole M.
$405 nightly
The price is $465
Nov 3 - Nov 4
Total with taxes and fees
Family-Friendly 3BR Apt - Easy Downtown Boston Accesss - near Franklin Park 603
A wooden front door with a glass panel and the number 383.

14. FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383

FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383
Quincy
9.8 out of 10, Exceptional, (53 reviews)
"Very cute property that was very clean, the host was extreme nice with great knowledge of the area and a prefect parking map!"
United States
Alicia R.
$300 nightly
The price is $335
Oct 6 - Oct 7
Total with taxes and fees
FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383
A kitchen with white cabinets, a tiled backsplash, and a knife block on the counter.

15. 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, (34 reviews)
"Our experience was excellent! The property was very clean, comfortable, and the accommodations were exactly as represented on the app. The property owner provided excellent instructions for our stay including entry, parking, and departure. We had one question upon arrival and the owner was immediately responsive. We would definitely stay again!"
United States
Kasey F.
$370 nightly
The price is $414
Oct 13 - Oct 14
Total with taxes and fees
Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41
A kitchen with white cabinets, a tiled backsplash, and a knife block on the counter.

16. 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, (54 reviews)
"Very clean and stay was enjoyable. "
United States
Sheldon S.
$378 nightly
The price is $423
Oct 13 - Oct 14
Total with taxes and fees
Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39
A neatly arranged bedroom with a bed, bedside tables, a dresser, and a window providing natural light.

17. 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, (58 reviews)
"Great overall stay!"
United States
Chris R.
$450 nightly
The price is $502
Oct 6 - Oct 7
Total with taxes and fees
Cozy three-bedroom home close to Boston w/ plenty of parking
A gazebo with a stone barbecue grill and a table with chairs.

18. Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
Dedham
9.0 out of 10, Wonderful, (70 reviews)
"Our stay was exactly what we needed while vacationing in Boston. Our host was gracious enough to even let us check in early. We had a ton of space and the beds were very comfortable. Would definitely stay again!"
United States
Cortney
$207 nightly
The price is $231
Oct 28 - Oct 29
Total with taxes and fees
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

19. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
8.8 out of 10, Excellent, (18 reviews)
"Cute place with a great location and responsive communication from the host. Would stay here again!"
United States
Lisa
$194 nightly
The price is $228
Nov 4 - Nov 5
Total with taxes and fees
Stunning Back Bay Studio Apartment
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, (1,299 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
$140 nightly
The price is $157
Nov 2 - Nov 3
Total with taxes and fees
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

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Restaurant Joia was excellent!!"
Nanette 2-night trip
Posted 1 hour ago
Harborside Inn Of Boston

Find out more about Milton

Everything you need to know about Milton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Milton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Milton vacation 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 low season months. For more hustle and bustle, you may prefer to visit Milton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $157 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Milton rentals

At Expedia, we put the best Milton vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Milton?

Yes, we give you a choice of vacation rentals in Milton near Blue Hills Reservation, or you can select a secluded option if you'd like a relaxing place to stay. Milton is known for its shopping and restaurants.

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

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This vacation 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a hot tub and a selection of books.

How many vacation rentals are there in Milton?

With 15 Expedia vacation rentals, you're sure 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 vacation rentals like in Milton?

Vacation rentals are privately owned accommodations you can book for several days or more in Milton. Vacation rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family trip.