Holiday houses 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

Apartment in Winthrop

4.96 out of 5 average rating, 301 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

HeatherRating, 5 stars2 months ago
Frank and Kathy are THE BEST! The space was perfect—so clean and comfy. It was also private and easy to access. My favorite feature: the heater in the bathroom! The location is also 700 feet from my best friend, so I will be back!!! Truly, this has been my best AirBnB experience ever.
Superhost

Condo in Plymouth

4.77 out of 5 average rating, 154 reviews

Clear Pond Pet Friendly Inn, Winter months 50% off

NicklausRating, 5 stars2 months ago
Friendly host! Allowed us to bring our 4 little dogs! Hard to find a host that will allow this. Clean and peaceful property.
Guest favourite

Home in Plymouth

5 out of 5 average rating, 106 reviews

Updated Antique in Historic Downtown Plymouth

AdrianaRating, 5 stars1 month ago
Matt's place was amazing! We stayed a week over the Christmas holiday and the home had everything that we could possibly need. The kitchen was fully stocked with lots of pots, pans, dinnerware and glassware. The beds were very comfortable and the bathrooms were spotless. The entire home was exactly what we needed to host Christmas with our daughters and granddaughter. We would absolutely stay here again. Thanks Matt for everything!
Guest favourite

Home in Plymouth

4.82 out of 5 average rating, 308 reviews

Historic 1 Bed/In Town/Best Location/Hot tub/deck

TravisRating, 5 stars1 week ago
Great location and stay. My wife and I felt very comfortable.
Guest favourite

Home in Scituate

4.95 out of 5 average rating, 19 reviews

Button Beach Cottage

Lawrence (Larry)Rating, 5 stars2 months ago
My family stayed over Thanksgiving 2024. The space was clean, pleasantly appointed and in a nice neighborhood. We would return.
Guest favourite

Apartment in Salem

4.98 out of 5 average rating, 374 reviews

Winter Island Retreat

AlexanderRating, 5 stars1 week ago
I would give 10 stars for the host if I could. I was lucky with all my AirBnB hosts, but David was exceptional - very fast communication, plenty of helpful suggestions, offered me himself to check in earlier and check out later then the standard time (as his circumstances allowed). The place itself is great - very clean, full of light, beautiful views, very quiet, private, short drive away from old Salem, stocked with everything you would need for morning coffee and cooking. Definitely great find! Thank you David!
Guest favourite

Apartment in Swampscott

4.89 out of 5 average rating, 104 reviews

Ocean views, Large Deck, Grill, Kid/Dog Friendly

LaurisaRating, 5 stars1 month ago
Perfect place to stay - sparkling clean, walking distance to the beach and to shops, gorgeous porch with ocean views & plenty of seating. Inside was comfy with high end finishes like marble, we loved using the gourmet 6 burner stove and large dining table. So many great things about this place, definitely recommend! Plus the host Ryan was super responsive & helpful.
Guest favourite

Tiny home in Greenville

4.97 out of 5 average rating, 672 reviews

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly

StephenRating, 5 stars2 weeks ago
This Airbnb was amazing and just what we were looking for! We were able to explore RI from this central location and enjoy all the local amenities! Corey was an amazing host and we loved the “Honor Bar” set up after our late night arrival. My wife, dog Bella and I would come back in a heartbeat!
Superhost

Home in Scituate

4.83 out of 5 average rating, 58 reviews

Sand Hills Beach - lighthouse area -

JordannaRating, 5 stars1 month ago
We had another great stay at Maria's. It was our third trip to her Airbnb. We always find her home super easy, clean, and comfortable. And Scituate is adorable. This time we had one small issue which Maria handled immediately - even at 10pm - and sent help that fixed the issue within an hour.
Guest favourite

Home in Scituate

5 out of 5 average rating, 20 reviews

Coastal Retreat

RachelRating, 5 stars1 week ago
Our stay at this lovely Scituate Coastal Retreat was fabulous. The house was immaculately clean and the decor was perfection. The common areas were cozy, but spacious and the kitchen was well stocked with any tools/utensils we needed. Beds were comfortable and our party of 4 adults had plenty of room. The hosts left great suggestions for local dining and the house was only a 2 min drive (15min walk) to downtown Front St restaurants and shopping. Host Andrew was very responsive and wonderfully accommodating, allowing for a later check-out when requested. We were staying in the Winter, so perhsps check out time may not be as flexible in the warmer months. Check-in & check-out was a breeze! We hope to rent this property again. Thank you Andrew & Madeline!
Guest favourite

Home in Plymouth

4.93 out of 5 average rating, 41 reviews

Serene Lakefront Retreat: Your Perfect Getaway!

CarolRating, 5 stars1 month ago
Minh took the time to decorate for the holidays. She was very responsive. Her place was Spotless! There were plenty of places to relax.
Guest favourite

Condo in Gloucester

4.96 out of 5 average rating, 100 reviews

Luxurious beach house w/ harbor views & near beach

KathleenRating, 5 stars3 months ago
Our stay in Gloucester was beyond amazing! A trip we have put off since Covid began but back in June we decided to make it happen! Sarah’s condo was beyond our expectations. Beautifully set up,homey, comfortable and right in the middle of the most beautiful views I’ve ever seen. We are from Annapolis, Maryland and I grew up on our bay crabbing … Gloucester reminds me of home. Everyone we met were so friendly, helpful and made sure we were comfortable. I’m a runner of 40 miles a week so my morning runs were filled with so much beauty from colorful leaves, to a sunrise I’ve never seen! Sailing is my thing so being surrounded by water, boats and of course the smell of fish … we knew our trip was extra special! We stayed specifically on Halloween for Salem fun and Salem did not disappoint! Helpful… a bar directly across the street from her air bnb! We hiked to the lighthouse early morning for exercise and its view did not disappoint either! Five star visit!

Popular amenities for Milton holiday rentals

Stay near Milton's top sights

Star Market81 locals recommend
Ashmont Grill56 locals recommend
South Shore Plaza55 locals recommend
Sophia's Grotto52 locals recommend
CVS49 locals recommend
Fornax Bread Company38 locals recommend

Other great holiday rentals in Milton

Superhost

Home in North End

4.8 out of 5 average rating, 20 reviews

Casa Mai

JessicaRating, 5 stars3 months ago
It was exactly what we expected, a clean spacious house that suited our needs for the weekend. It was a close drive into the center of Providence, as well as walkable pizza joints. There were 4 individual bedrooms and a sofa bed that fitted everyone. We felt comfortable and safe in the area. Jasmin responded to any questions and was polite and helpful all the time.
Superhost

Guest suite in Burlington

4.74 out of 5 average rating, 50 reviews

Lovely Two Bedroom Home in Burlington

JohnRating, 5 stars3 months ago
Paul was a gracious host. Friendly, accommodating and undersanding. I'll definitely book again
Superhost

Cabin in Plymouth

4.82 out of 5 average rating, 1,015 reviews

Traditional Log House Near Cape Cod/Boston

TarahRating, 5 stars5 days ago
We booked this place for a romantic anniversary dinner. If you’re looking for cozy and romantic, I would definitely recommend. The nice wood and kind of remote location made it very nice. We walked in to fireplaces on the TV and romantic jazz. Well decorated and lovely. We had what we needed to cook dinner and there was a table available to eat. The bed is quite comfortable and the accommodation was warm and cozy. We were only there for a night so we didn’t get to enjoy the views but I’m sure they are great. If you read the description, it accurately describes everything including a few repairs the host is working on getting done. We didn’t hear any mice or squirrels. Only regret was not booking for another night.
Superhost

Apartment in North End

5 out of 5 average rating, 4 reviews

Modern and spacious lovely home

ManjushaRating, 5 stars1 month ago
We had a wonderful stay at this place! The property was exactly as described – clean, cozy, and in a perfect location. Host was incredibly friendly and responsive, and checking in to make sure everything was going well. The extra touches, like fresh towels and snacks, really made a difference. Highly recommend this place for anyone visiting Providence, RI. Would definitely stay again!
Guest favourite

Cottage in Lincoln

5 out of 5 average rating, 39 reviews

Fully equip cottage,1 night welcomed w fenced yard

AlexRating, 5 stars1 week ago
stayed here a few times now and Donna has been a fantastic host. always responsive and helps with anything you need. felt right at home and would recommend to anyone staying in the area
Guest favourite

Apartment in Brighton

4.99 out of 5 average rating, 74 reviews

New 3 bedroom, 2 bath unit, meadow view!

EvaRating, 5 stars3 weeks ago
We had a wonderful time staying in this apartment for a week. Simon's apartment is extremely neat, comfortable, and well-organized. He was very thoughtful, preparing chocolates, oranges, various beverages, and even a bunch of roses for us. I highly recommend this place. When I visit Boston next time, I will definitely choose to stay here again.
Superhost

Guest suite in Arlington

4.85 out of 5 average rating, 82 reviews

★Modern Studio-Private Entrance,Washer+Dryer★

BrianRating, 5 stars1 month ago
Had a great stay at this place (this was our second time there). Our plane to the area was much delayed but our hosts were understanding and very helpful. Everything was as advertised and the place was convenient to our activities visiting family. Will definitely stay there again!
Guest favourite

Apartment in Swampscott

4.98 out of 5 average rating, 40 reviews

Ocean View Apartment 2nd Floor

SherylRating, 5 stars3 months ago
We have had a lot of luck with AirBnB, but Valeri's place was the best so far. Literally across the street from beach access. A great restaurant next door with several others in easy walking distance. Minutes from Salem and Marblehead. The rental was fantastic. You could and picture it as being what you would want in a seaside vacation getaway or second home. Everything was clean, stocked, and organized. Beds were comfortable, and it was just a really all around relaxing environment. Loved the decor! Valeri was very nice and gave great local recommendations. I don't check to see if she's a "super" host, but she's number one for me. Loved our weekend getaway and would absolutely book again.

Quick stats about holiday rentals in Milton

  • Total rentals

    130 properties

  • Nightly prices starting at

    $48 AUD before taxes and fees

  • Total number of reviews

    4.6K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

Destinations to explore

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