Holiday rentals in Milton

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Top-rated holiday rentals in Milton

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A bright and airy room features a comfortable bed adorned with colorful bedding. Two wooden desks with chairs are positioned thoughtfully, along with various seating options. Natural light filters through a window, accentuating the room's warm wood flooring and blue walls.
Guest suite in Boston
4.9 out of 5 average rating, 172 reviews

Boston arbor oasis - cute one bedroom suite

Upbeat, beautiful one bedroom with attached bathroom. Have the ground floor / lower level of our home to yourself. Your own private entrance, come and go as you like. Located on a quiet, dead end street in a very safe, residential Boston neighborhood, with big beautiful evergreen trees. Convenient to 93. Five minute Uber or short bus ride to Ashmont station, from here take the train downtown Boston. Free off street parking. Easy walk to coffee shops, restaurants, bars, and Neponset River trail!

Top guest favourite
A spacious master bedroom is depicted, featuring a large bed with crisp white linens. Rich, dark curtains frame tall windows, complementing the soft pink walls. A modern television is mounted on the wall, and mirrored doors reflect the inviting decor, enhancing the room's brightness.
Guest suite in Ashmont
4.96 out of 5 average rating, 267 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A unique master bedroom and a cozy 2nd bedroom adjacent to a marble spa bathroom (with heated floor and a large shower & built-in bench). With a clean, glass-tiled kitchen & granite-top counters, you’ll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood. Enjoy the feel of a downtown hotel without the high price. Note: There’s no separate living room, but comfortable seating is available in the 2nd bedroom & kitchen

Top guest favourite
A spacious studio features a comfortable bed with a decorative pillow against the warm wood headboard. Soft, natural light fills the room, highlighting the wooden floors and cozy seating area. A kitchenette is visible in the background with cabinets and a small coffee setup.
Guest suite in Jamaica Plain
4.92 out of 5 average rating, 244 reviews

Ann and Esther's Cozy Studio near the Heart of JP

This airy and light private studio is set in a beautiful, secluded backyard/garden. Close to restaurants, shops and acres of green space. Your reservation confirms that you have read "Other Things to Note" in The Space section below and "House Rules" before booking. Guests can only book for themselves. We are 5-7 minutes from the 39 bus and 15 from the Orange line. There is microwave, fridge, counter w/ sink. No stove or cooking. DO NOT request >6 mos ahead. Insta-Book when calendar opens

Guest favourite
A newly remodeled kitchen features modern stainless steel appliances and ample counter space. White cabinetry contrasts with warm wood paneling and flooring. A dining area with a wooden table and chairs is visible, along with soft lighting from pendant fixtures above.
Cabin in Cohasset
4.92 out of 5 average rating, 363 reviews

Lionsgate at Cohasset

Lionsgate is the perfect retreat to refresh the soul. Newly remodeled fully stocked kitchen with comfortable amenities provide a home away from feel. Enjoy a roaring fire in a rustic cabin during the winter or the coolness of a mini split in the summer. Cohasset, jewel of the South Shore is a quintessential New England seaside village located half way between Boston and Cape Cod. The ocean offers abundant recreation opportunities as well as plentiful parks for hiking and biking. A must visit.

Top guest favourite
An open living and dining area is highlighted by a wooden dining table set with decorative plates. The space features grey upholstered chairs and a cozy seating arrangement with light-toned furniture. A circular chandelier hangs above, while exposed brick accents add texture to the room.
Flat in Ashmont
4.96 out of 5 average rating, 145 reviews

🎖The Ashmont Suite | Close to Subway + Downtown🎖

This high end & unique 3 bed / 2 bath unit is brand spanking new, along with all the furnishings. It includes 1 King, 1 Double, & 1 Single size private bedrooms. The unit is extremely clean and remarkably decorated. Only a 5 minute walk to Ashmont station (red line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. There are two great restaurants nearby - Molinari’s and Tavolo, as well as a local coffee shop & a Dunkin just across the T Station.

Top guest favourite
Townhouse in Somerville
4.96 out of 5 average rating, 157 reviews

Modern Somerville Cottage

My place is a beautiful new house located in the Hip neighborhood of Davis Sq in Somerville. Conveniently on the bike bath leading to Davis Sq with its T stop and all its great restaurants and bars (15 min walk). 2 Mins walk to the new Green line extension that takes you to Cambridge and Boston. Modern furnishings throughout with amazing light from all sides and double height cathedral ceilings in the living/dinning room. I also have 2 beautiful condos in Killington VT please ask for info

Top guest favourite
A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.
Place to stay in Sherborn
4.98 out of 5 average rating, 324 reviews

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

Guest favourite
A modular queen sofa with light blue upholstery is positioned in a brightly colored living area. Vibrant patterned cushions enhance the seating, while an ottoman and area rug with a similar design add comfort and style. The kitchenette and additional furnishings are visible in the background.
Flat in Randolph
4.86 out of 5 average rating, 123 reviews

TLC Boston- private unit in family home.

One bedroom unit, with a well decorated open space living room area. Queen bed and queen modular sofa and optional air bed. 15 miles from Logan Airport and located just .2 miles once you exit the highway. Convenient highway access to Boston, Foxboro Stadium, and Cape Cod. Short distance to the Blue Hills hiking trails, shopping mall, shopping centers, and restaurants. Few blocks walk to bus stop to access public transportation into Boston. A diverse community and family friendly!

Guest favourite
A full kitchen is featured, showcasing a large granite counter with seating and a blend of modern appliances, including a gas stove and refrigerator. Exposed brick walls add texture, while natural light enters through windows, creating a bright and functional space.
Flat in Roxbury
4.8 out of 5 average rating, 189 reviews

A King Bed | Apartment | Middle of Boston

Located in the geographical middle of Boston you can get to anywhere in the city within 20 minutes including Harvard/MIT, Downtown, Fenway, Hynes Convention Center, Seaport and more. This pseudo apartment on the first floor is separate from the rest of the house and has its own private entrance, a private bathroom and a dedicated off street parking spot. The full kitchen with oversized counter is great for eating; comfy living room for relaxing and an office nook for working.

Guest favourite
A modern kitchen is visible, featuring stainless steel appliances, including a gas stove and a large kitchen sink. A dining table made of dark wood is surrounded by red metal chairs, providing a casual dining option. Natural light fills the space through a large window.
Flat in Wollaston
4.95 out of 5 average rating, 282 reviews

Luxury, Location, Privacy. Walk to train. Boston

Luxury. Convenient. Short walk to train. 5 stops to South Station, The main station in Boston. Short walk to stores, restaurants. All brand new. Full gut renovation. Parking spot right outside your private entrance. This is a true getaway. Washer and Dryer also in unit. Beautiful park right across the street. One bedroom unit with a pullout couch in living room.

Top guest favourite
A historic brick brownstone is shown from the street, featuring a classic architectural style with bay windows. The building is framed by vibrant green trees and neatly trimmed bushes, contributing to the residential charm of the neighborhood.
Apartment in Jamaica Plain
4.89 out of 5 average rating, 577 reviews

Historic JP Brownstone with Parking. Pets Welcome!

Located in one of Boston's best neighborhoods, this 1200 square foot bright sun filled corner unit in a 120 year old historic Brownstone is the perfect retreat. Its excellent location is just steps from the T and a short walk to Centre Street shops and restaurants. Good for couples, solo adventurers, business travelers, and furry friends (pets).

Guest favourite
Apartment in Norwood
4.8 out of 5 average rating, 106 reviews

The Plant Haus

A peaceful oasis with easy access to Rt 1, Rt 128, and walking distance from Norwood Center and the Norwood Depot commuter rail stop that goes to South Station. 30 mins from Providence and Boston and less than 20 mins to Gillette Stadium. My place is located in a quiet community. I am just a phone call or text away should you need me!

Popular amenities for Milton holiday rentals

When is the best time to visit Milton?

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Avg. price$151 SGD$148 SGD$161 SGD$179 SGD$179 SGD$193 SGD$189 SGD$196 SGD$184 SGD$180 SGD$179 SGD$169 SGD
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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Milton?

    Yes! Work meets play with ease at over 90 vacation rentals in Milton featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Milton have free parking?

    Absolutely! We offer over 40 house rentals with free parking in Milton. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Milton?

    Make yourself at home in Milton by choosing from our most frequently booked neighborhoods. We have over 310 vacation rentals in Hyde Park, over 2,650 vacation rentals in Montclair, and over 310 vacation rentals in Stony Brook - Cleary Square.

  • Are there family-friendly vacation rentals in Milton?

    Milton has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do hotel rentals in Milton have wifi?

    Absolutely! We offer over 10 hotel rentals with wifi in Milton. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Milton?

    Four-legged friends are welcome in Milton. Choose from more than 50 vacation rentals for guests traveling with pets.

  • What are the most popular amenities for Apartment Rentals in Milton?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 60 homes with air conditioning, over 40 homes with free parking, over 60 homes with a kitchen, over 60 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • How much does it cost to stay in apartment rentals in Milton?

    Experience the best of Milton with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Milton have a kitchen?

    Absolutely! We offer over 60 apartment rentals with a kitchen in Milton. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Milton have air conditioning?

    Absolutely! We offer over 50 house rentals with air conditioning in Milton. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Milton

  • Total holiday rentals

    Explore 150 holiday rentals in Milton

  • Nightly prices starting at

    Milton holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,910 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    150 of Milton holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Milton rentals

  • 4.7 Average rating

    Milton stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Milton’s top spots include Milton Station, Central Avenue Station and Butler Station

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