Holiday rentals in Boston
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Top-rated holiday rentals in Boston
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Flat in Boston
4.89 out of 5 average rating, 247 reviews🎖The Boiler Room | Close to Subway + Downtown🎖
This unique private suite is brand new & comes w/ its own private entrance. Including a queen size bed, ensuite bathroom, & a wine/craft beer minibar! The unit is extremely clean and very nicely decorated. A quick 5 minute walk to Ashmont Station (Red Line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. Great restaurants nearby - Molinari's & Tavolo Ristorante - as well as a local coffee shop + a Dunkin just across the Ashmont metro station.
21–28 Dec
Guest suite in Boston
4.96 out of 5 average rating, 201 reviewsUpscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry
The home is a short 7 minute walk to Ashmont T Stop. A truly unique master bedroom and a cozy 2nd bedroom both adjacent to a marble spa bathroom (which has a heated floor and a large shower with a built in bench). With a clean, glass-tiled kitchen with granite-top counters, you'll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood perfect for romantic couples, solo adventurers, and savvy business travelers who want the feel of a downtown hotel without the high price.
10–17 Nov
Guest suite in Boston
4.91 out of 5 average rating, 193 reviewsCozy Private Garden Studio near the Heart of JP
Best of both worlds: this airy and light, newly renovated private studio is set in a beautiful, secluded backyard/garden. Easy walk 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 a microwave, fridge, counter and and sink but no stove or cooking options.
25 Aug – 1 Sept
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Boston holiday rentals
Other great holiday rentals in Boston
Flat in Cambridge
4.93 out of 5 average rating, 242 reviewsBright Convenient Apt Harvard / MIT
10–17 Mar
Flat in Cambridge
4.94 out of 5 average rating, 315 reviewsprivate studio near Harvard/MIT
18–25 Feb
Guest suite in Norwell
4.95 out of 5 average rating, 258 reviewsPrivate suite South Shore
30 Apr – 7 May
Flat in Boston
4.84 out of 5 average rating, 302 reviewsBeacon Hills Studio next to State house
4–11 Dec
Flat in Boston
4.91 out of 5 average rating, 144 reviewsArtistic charm in hip J.P.
21–28 Apr
Flat in Revere
4.87 out of 5 average rating, 257 reviewsBeachside Cozy Space-Near Boston/Airport/Train
15–22 Feb
Guest suite in Everett
4.92 out of 5 average rating, 216 reviewsBasement Apartment in prime location near Boston
22–29 Mar
Flat in Waltham
4.98 out of 5 average rating, 209 reviewsCozy Private Studio Unit w/ Laundry and Parking!
23–30 Sept
Apartment in Boston
4.95 out of 5 average rating, 168 reviewsCITY APARTMENT NEAR AIRPORT
1–8 Feb
Guest suite in Rockport
4.99 out of 5 average rating, 605 reviewsHalibut Point State Park. Nature Lovers Retreat
26 Feb – 5 Mar
Flat in Lowell
4.96 out of 5 average rating, 128 reviewsPrivate Master & Living Room! Entire Space!
2–9 Apr
Flat in Natick
4.98 out of 5 average rating, 330 reviewsScandi-Modern Apartment
8–15 Sept
Quick stats about holiday rentals in Boston
Total rentals | 9K properties |
---|---|
Rentals with dedicated workspaces | 4.6K properties have a dedicated workspace |
Rentals with a pool | 490 properties have a pool |
Pet-friendly rentals | 2.5K properties allow pets |
Family-friendly rentals | 3.1K properties are a good fit for families |
Total number of reviews | 386K reviews |
Your guide to Boston
All About Boston
As one of the United States' oldest settlements, the New England city of Boston is thick with history. Downtown's mazelike map of one-way streets alludes to a time when travel meant horseback, and you can still wander the well-worn cobblestone pathways that ribbon through Beacon Hill — Acorn Street is an especially popular photo op. Harvard University in Cambridge has been around since 1636, and Boston Harbor still hosts reenactments of its infamous Boston Tea Party.
But history isn’t the only reason to visit the capital of Massachusetts. There are baseball games at Fenway Park, exhibits to explore at the Museum of Fine Art, and picnic opportunities at Boston Common. Next to the Common, the Public Garden features leisurely rides on the paddle-operated Swan Boats, operating on the pond since 1877.
Cocktail bars and creative cafes serve up drinks on both sides of the Charles River. For freshly shucked oysters and Boston clam chowder, downtown is hard to beat.
The best time to stay in a holiday rental in Boston
Boston enjoys a temperate East Coast summer, with warm — but not too hot — weather that’s perfectly suited for outdoor activities. It’s an excellent time to go sailing on the harbour, grab lunch in the sunshine, or wander through Downtown Boston. Boston Harborfest — one of the biggest Independence Day celebrations in the States — takes over around the Fourth of July, with fireworks, live music, and an assortment of historical family-friendly events.
Autumn starts in September, cloaking the city in red and orange leaves and kicking off the annual Boston Film Festival. Boston’s winters live up to their frosty reputation, but you can thaw out with a skate at the Boston Common Frog Pond or grab a winter warmer at a cosy pub near the many cottages in Boston. Spring remains chilly, but it’s worth layering up to watch one of the most competitive marathons in the country in April.
Top things to do in Boston
Isabella Stewart Gardner Museum
This museum houses more than 7,500 paintings, ceramics, sculptures, and other works of art, plus thousands of rare books and archival objects — all curated by its original owner, Victorian collector Isabella Stewart Gardner. Upon her death, she dedicated the building and its exhibitions “for education and enjoyment of the public forever.”
Boston Public Market
Quincy Market may get more press, but the Boston Public Market is arguably more intimate, with tens of shops instead of hundreds. As an indoor market, it’s also open year-round, with independent sellers hawking chocolates, doughnuts, fish, and honey — all grown, caught, or made locally in Massachusetts.
Blue Hills Hiking
Just 15 minutes from downtown, the Blue Hills Reservation offers 200 kilometres of trails through Massachusetts hills and meadows. Hikes run the gamut from gentle walks like Houghton’s Pond Loop — an especially gorgeous route in autumn — to mountain climbs up to Buck Hill and Skyline. You’ll also find cross-country ski routes available in winter.
Destinations to explore
- Cape Cod Holiday rentals
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