House holiday rentals in Milton

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Milton

House rentals with a pool

Superhost
Home in Gloucester
4.73 out of 5 average rating, 15 reviews

Mansion in Gloucester with Pool

MaryRating, 5 stars6 months ago
My family and I were fortunate enough to spend the thanksgiving holiday here. It was the perfect space for a group gathering. Would highly recommend!
Top guest favourite
Home in Newton
5 out of 5 average rating, 19 reviews

Villa with private Pool in Boston's Elite Enclave

JonRating, 5 stars3 weeks ago
Great option when staying in Newton and right down the street from an incredible entrance to a hiking trail. Serge was a great host and kept us informed the entire trip.
Top guest favourite
Home in Lakeside Marblehead
5 out of 5 average rating, 17 reviews

Large Pool, Nature Trails, Redd's Pond, 4-Bed

AlanaRating, 5 stars3 weeks ago
Amy was very responsive and communicative. The house was clean and maps took us right to the home. It was too early in the season to enjoy the pool but it was pristine and would have been great for hot summer weather. Amy was wonderful with trying to accomodate any requests and we liked the location from easy access to Salem and within a one hour drive to Boston!
Guest favourite
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

DeanneRating, 5 stars6 days ago
Brad was very friendly and helpful. Beautiful home!
Top guest favourite
Home in Arlington
4.94 out of 5 average rating, 34 reviews

Beautiful Spacious 4BRM House!

NicholasRating, 5 stars2 weeks ago
I loved everything Maxine said and how she helped navigate around every even in the house, everything was so clean, very quite place good for professional working, everything was just beyond, amazing & lovely place you feel right at home with so much space to move around the house. Being free having your privacy. Thank you Maxine 🙏👏🏽
Top guest favourite
Home in Norwood
4.95 out of 5 average rating, 44 reviews

the house of id; vintage shop, accessible space

JasonRating, 5 stars1 week ago
Super fun and eclectic house! What really made the stay were the owners, they are thoughtful and very responsive, they clearly care a lot about their guests!
Guest favourite
Home in Weston
4.97 out of 5 average rating, 95 reviews

Spacious vacation unit in premium suburban town

LucyRating, 5 stars3 weeks ago
Scott was very easy to communicate with, and he was very nice. They were so thoughtful and even left us a dozen eggs from their backyard chickens! The place was spacious and peaceful. Check in and checkout process was very easy!
Superhost
Home in Plymouth
4.63 out of 5 average rating, 139 reviews

Harlow Bishop House walk to ocean in town, hot tub

TerriRating, 5 stars1 week ago
Our accommodations were beyond what we expected. The location was perfect. Restaurants and shops were within walking distance, and we felt right at home. Our space was comfortable and clean. We will be back!

Weekly house rentals

Guest favourite
Home in Brockton
4.96 out of 5 average rating, 50 reviews

Leisure | Business| Getaway| Downtown Brockton

ValeriaRating, 5 stars1 week ago
Immaculate home with everything provided and so easy to just arrive and feel at home. Sheets and towels were immaculate and clean so was the rest of the home!!!!!! Beautifully decorated!!!!
Superhost
Home in Quincy
5 out of 5 average rating, 3 reviews

Studio w seaside deck access

GarlandRating, 5 stars3 months ago
This is my third booking at Kay's place. That should say enough when there are many other choices.
Guest favourite
Home in Roslindale
4.99 out of 5 average rating, 76 reviews

Upscale Boston 2 BR w/ Off Street Parking

LindaRating, 5 stars2 weeks ago
Pristine clean, great beds, comfortable, onsite parking, safe
Guest favourite
Home in Dorchester
4.94 out of 5 average rating, 97 reviews

New Spacious Home in Boston

HannahRating, 5 stars2 days ago
We celebrated our bride to be at this airbnb and it was the perfect place to do so- clean, spacious, modern and stocked with just about every amenity you could need! Esther was responsive and kind. When we went to downtown Boston, we took 20 minute drives with Uber, which was very convenient for us. The driveway parking and street parking was also very helpful for our group. Would highly recommend this airbnb!
Superhost
Home in Randolph
4.84 out of 5 average rating, 79 reviews

The Adelaide Guest House, Minutes from Boston

NoraRating, 5 stars4 weeks ago
Perfect spot for our family for a weekend event at Gillette Stadium and a day in Boston. Convenient location, clean, lots of space and very comfortable.
Guest favourite
Home in Roslindale
4.9 out of 5 average rating, 31 reviews

Kailyn Apartment Boston, Massachusetts

AngelaRating, 5 stars1 week ago
Egla’s place was great for our overnight stay! Communication was excellent! It was very clean, quiet, and comfortable. We appreciated the provided snacks and beverages. Thanks for a great stay!
Top guest favourite
Home in Brockton
5 out of 5 average rating, 34 reviews

Last-Minute Deal: Spacious, Deluxe and Cozy Stay!

MarieRating, 5 stars5 days ago
⭐️⭐️⭐️⭐️⭐️ 5/5 – A Perfect Stay with a Wonderful Host! I had an outstanding experience staying at Joe’s Airbnb on Herrod Ave in Brockton. From the moment I arrived, it was clear that Joe is a thoughtful and attentive host who genuinely cares about her guests' comfort and experience. The home was spotless, beautifully maintained, and exactly as described, if not better. Every detail was thoughtfully arranged, from the cozy linens and fully stocked kitchen to the fast Wi-Fi and quiet surroundings. The neighborhood is peaceful and safe, and it's conveniently located near shops, restaurants, and major routes. Joe was incredibly welcoming and responsive throughout my stay. She made sure I had everything I needed, offered great local tips, and went above and beyond to ensure I felt right at home. Whether you're visiting Brockton for business or leisure, I can't recommend this place enough. If you’re lucky enough to find availability here, don’t hesitate, book it! Thank you again, Joe?
Guest favourite
Home in Randolph
4.98 out of 5 average rating, 54 reviews

Convenient and spacious Home w/ 4BR 2.5BA

LloydRating, 5 stars3 weeks ago
My first Airbnb experience. All went well. Hopefully any future experiences will live up to the high standard that Roger has set. Will stay there again if the opportunity arises. Great experience. Thanks Roger!!

Private house rentals

Top guest favourite
Home in Greater Mattapan
4.98 out of 5 average rating, 61 reviews

Brand New 4BR 2.5Bath House 20Min Downtown Boston

JayRating, 5 stars1 week ago
The house was very clean and exactly as the pictures looked. It is stocked with everything you'll need, soap, paper towels, silverware, etc... There are lots of small restaurants within walking distance, pretty much any type of food you could want. Pamela was great, and very easy to communicate with. It was an extremely easy check-in and check-out.
Top guest favourite
Home in Wellesley
5 out of 5 average rating, 41 reviews

Elegant Guest suite Wellesley

AndreaRating, 5 stars4 days ago
We had a great stay. This home has all the comforts of home and is conveniently located. The host is wonderful and gracious and communicates back almost instantly with answers to questions. The shower was fantastic and the espresso maker and pods were better than ours at home. Linens and everything about this home feels upscale and luxurious. There's a little traffic noise during the day but the high quality windows keep it pretty quiet and it's quiet at night. Lots of great shops and restaurants nearby and easy easy to get everywhere. So green and pretty too. We really enjoyed our stay.
Guest favourite
Home in Dorchester
4.96 out of 5 average rating, 28 reviews

Modern 5BR | Near Subway & Downtown | Free Parking

CarolineRating, 5 stars2 weeks ago
We had a fantastic stay at Hiep’s place! The house was spotless, spacious, and thoughtfully set up with everything we needed, from a fully stocked kitchen to fresh towels and toiletries. The home felt newly renovated and was perfect for our group, with plenty of room to relax and enjoy meals together. The location was super convenient, it was just a 5-minute walk to the Ashmont T station and easy access to downtown Boston. Despite being in the city, the neighborhood felt quiet and safe. What truly made the stay exceptional was Hiep's hospitality. He was incredibly responsive, accommodating, and went above and beyond to make sure we were comfortable. You can tell he genuinely cares about his guests' experience. Highly recommend this place for families, group trips, or work retreats. We'd absolutely stay again!
Guest favourite
Home in Jamaica Plain
4.96 out of 5 average rating, 83 reviews

Beaut private close univ+hospital

MaryRating, 5 stars2 weeks ago
Had a lovely stay at the apartment. It is spacious and is in a convenient location about 10 min walk to subway and could easily use public transport to get to points of interest in 15-30 min. Close to several parks/greenspaces and good restaurants. Maria is a very helpful, considerate, and polite host.
Top guest favourite
Home in Marshfield
5 out of 5 average rating, 18 reviews

Beach Break -3 BR- Walk to Beach

JackieRating, 5 stars9 months ago
We just wrapped up our second stay at "Beach Break" and again, from the moment we arrived, we were in total heaven. The entire property is squeaky clean and the location is superb – just a short stroll to the beach. Stefanie and Dave have created a total gem. Their dedication to providing an exceptional experience is evident in every detail. The space is incredibly beautiful, so much so that folks walking by stopped to comment on the well-cared-for exterior. We'll absolutely book again. This is truly a rare find.
Guest favourite
Home in Weymouth
4.85 out of 5 average rating, 54 reviews

City vibes in the suburbs.

ChrisRating, 5 stars2 weeks ago
Very clean, comfortable and homey place to spend a weekend. Much better than a hotel. Host was very easy to deal with. And bonus, it came with a very friendly dog who visited us at the back door often for ear scratches and pets.
Top guest favourite
Home in Scituate
5 out of 5 average rating, 6 reviews

BOOK NOW! Beathtaking Ocean front Estate w/HotTub!

DanielRating, 5 stars2 weeks ago
This property was beautiful. We had the greatest time ever! Thank you to Kimberly for being an awesome host. We would love to return to this property if we are in the Boston area :) 10/10
Top guest favourite
Home in Hull
4.97 out of 5 average rating, 31 reviews

4 bd Ocean View, Dual Deck, Beach Front Retreat

KamilRating, 5 starstoday
We had a blast at this property. The location is perfect and the house was exactly as pictured. The hosts are very flexible and accommodating!

Quick stats about house rentals in Milton

  • Total rentals

    50 properties

  • Nightly prices starting at

    $39 SGD before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 properties include access to wifi

Destinations to explore

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  5. Milton
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