Holiday rentals in Boston
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Top-rated holiday rentals in Boston
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Popular amenities for Boston holiday rentals
Other great holiday rentals in Boston
Flat in Woburn
4.96 out of 5 average rating, 105 reviewsComfy-Spacious-private 1BR conveniently located
10–17 Mar
Apartment in Boston
4.82 out of 5 average rating, 177 reviewsStylish garden level studio with a private patio
10–17 Jan
Flat in Boston
4.89 out of 5 average rating, 251 reviews🎖The Boiler Room | Close to Subway + Downtown🎖
10–17 Mar
Flat in Boston
4.95 out of 5 average rating, 115 reviewsQuirky studio in Jamaica Plain
4–11 Jul
Flat in Waltham
4.98 out of 5 average rating, 209 reviewsCozy Private Studio Unit w/ Laundry and Parking!
24–31 Dec
Flat in Boston
4.88 out of 5 average rating, 491 reviewsSerene Studio in a Perfect Location
6–13 Jul
Flat in Watertown
4.88 out of 5 average rating, 326 reviewsPrivate studio close to Boston and Harvard square
16–23 Mar
Flat in Natick
4.98 out of 5 average rating, 331 reviewsScandi-Modern Apartment
29 Sept – 6 Oct
Quick stats about holiday rentals in Boston
Total rentals
9.1K properties
Rentals with dedicated workspaces
4.7K properties have a dedicated workspace
Rentals with a pool
490 properties have a pool
Pet-friendly rentals
2.6K properties allow pets
Family-friendly rentals
3.2K properties are a good fit for families
Total number of reviews
388K 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
- Martha's Vineyard Holiday rentals
- Cambridge Holiday rentals
- Portland Holiday rentals
- Nantucket Holiday rentals
- Salem Holiday rentals
- Newport Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Montreal Holiday rentals
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