Discover a selection of 500 vacation rentals in Chelsea, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $160 per night, and houses and condos are popular options for a stay in Chelsea. Either way, you'll find a rental for everyone's needs.
Destination guide

Chelsea is a thriving riverfront community

Located just across the mighty Mystic River from bustling Boston, Chelsea is both a great base from which to explore the iconic Massachusetts metropolis, and a vibrant destination in its own right. Multicultural and densely populated, this compact city is dotted with handsome historical buildings, eclectic eateries, boutique breweries, and picturesque parks. With an extensive array of Chelsea vacation rentals to pick from, you're bound to find one to suit your needs and wants. And should you ever need a change of scenery, the cavernous museums, majestic monuments, and revered cultural venues of Boston are all just a stone's throw away.

Things to do

Chelsea's historical homes and pristine parks

You'll find an array of attractions within easy reach of your Chelsea vacation rental. For a compelling trip back in time, be sure to stop by the Governor Bellingham-Cary House Museum. Built in 1659, it's one of the most beautifully preserved and historically significant buildings linked to the founding of the Massachusetts Bay Colony. Friendly local experts will be all too happy to give you a guided tour, but opening hours are limited, so be sure to check listings before you visit. Mary O'Malley State Park is a lush, green riverside park with spectacular views of the Boston and Charlestown skylines. From here you can also marvel at the handsome Tobin Bridge, which connects Chelsea to Boston.


Spa days and indulgent nights in Chelsea

Massachusetts boasts a thriving craft beer scene, and Chelsea is home to boutique breweries and tap rooms, where you can sample all manner of lovingly made pale ales, porters, and stouts. If you're after a more virtuous form of self-indulgence, there are also tranquil spas, where you can treat yourself to an invigorating massage, or a traditional Russian steam bath. And no visit to Chelsea is complete without an aquatic adventure or two. Take a leisurely sunset cruise around handsome Boston harbor, race down the Mystic River in your own mini speed boat, or embark on a whale-watching expedition.


Enjoy 4 distinct seasons in Chelsea

Chelsea experiences a wide range of weather conditions over the course of each year. Summer days are long, warm, and sunny, which means that Chelsea vacation rentals are in high demand between June and August. Early fall brings a crispness to the air, but temperatures usually remain pleasant until November. You'll need to wrap up warm if you're visiting in winter, although the temperature tends to hover around freezing, rather than plunge too far beneath it. Snowfall is highly variable from year to year, but certainly a common occurrence between December and February.

Natural features

Whale watching and fall foliage in Chelsea

If you want to escape the hustle and bustle of the city, you'll find an abundance of natural spectacle within easy reach of Chelsea. If you're visiting between March and November, you can hop on a high-speed catamaran bound for Stellwagen Bank Marine Sanctuary, where you're very likely to catch a glimpse of several species of whales. If you're visiting in fall, Massachusetts is a prime spot for leaf peeping. Hire a car and take an unforgettable trip through the countryside, marveling at forests full of radiant red and glowing golden trees.

How to get there

Transportation options to and around Chelsea

Fly into Boston, MA (BOS-Logan Intl.), the closest airport, located 2.2 mi (3.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Bedford, MA (BED-Laurence G. Hanscom Field), which is 13.8 mi (22.2 km) away.

If you'd rather travel by train, the main station is Chelsea Station.

How many vacation rentals are available around Chelsea, MA?

Our 2020 property listings offer a large selection of 726 vacation rentals around Chelsea. From 113 house rentals to 532 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a city-center property in Chelsea?

There are so many reasons to stay someplace central when you go on vacation in a new city, but you can't argue with the number one draw — location, location, location! Vrbo has 117 city center rental properties available. Of course, that might not suit everyone. Luckily, Vrbo has a bunch of other options, including:

  • 31 seaside vacation rentals.
  • 28 ocean-view vacation rentals.
  • 25 beach vacation rentals.

Can I rent an apartment in Chelsea?

If you want to know how the locals live, pull back the curtains and soak up this destination from the comfort and convenience of an apartment. You'll be able to choose from 267 different options on Vrbo. If you book quickly, you could spend as little as $38 per night. Or perhaps you'd rather pick one of the area's other lodging types, such as:

  • Hotel: 134 vacation homes. Prices start from $28 per night.
  • House: 97 vacation homes. Prices start from $58 per night.
  • Condo: 78 vacation homes. Prices start from $98 per night.

Can I stay in Chelsea in a large group?

There's nothing quite like catching up with old work colleagues or spending a week or so with extended family in a fantastic new area. And the best thing, Vrbo has places to suit you. Apartment vacation homes are the preferred option for big groups of guests, with 33 listed here. Rental properties around here that are perfect for large groups include:

  • If yours is a group of 6, we offer 158 vacation homes perfectly suited for that size. Book a night from just $90.
  • If you have 5 in your crew, you'll be happy to find out that there are 138 vacation homes suitable. You can book one for as little as $91 per night.
  • Organizing a trip away with 8 guests? We offer 94 vacation homes that will meet your needs. Prices start from $145 a night.

You and your posse will be well looked after when you plan your Chelsea travels with us!

Where are the cheapest rentals in Chelsea?

Say au revoir to sterile, drab chain-hotel rooms! Indulge in the charm of living like one of the locals in an affordable rental instead. Feast your eyes on the unique options that can be snapped up now on Vrbo. Jamaica Plain has bargain written all over it. And with 157 Vrbo rentals at an average price of $283 a night, it's not hard to see why. Another 167 Vrbo rentals are available in or around Charlestown. With an average price of $296 a night, you're sure to grab a deal worth bragging about.

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