What are the top vacation rentals in Boston?

There are a lot of options in Boston. If you plan on staying in the Boston area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Boston: <a href="/property/luxurious-2br-2bath-with-outdoor-courtyard-and-garage-in-downtown-bardstown/HA-321847782" class="class="static-page-link"">Luxurious 2BR/2Bath with Outdoor Courtyard and Garage in Downtown Bardstown</a> <a href="/property/beautiful-decorated-apartment-located-in-the-heart-of-downtown-bardstown-ky/HA-3211431760" class="class="static-page-link"">Beautiful Decorated Apartment located in the heart of Downtown Bardstown, KY</a> <a href="/property/hayjac-house-perfect-downtown-location-and-the-living-is-easy/HA-1217165243" class="class="static-page-link"">HayJac House - Perfect Downtown Location and the Living is Easy.</a> <a href="/property/ron-orline-s-home-park-at-the-door-use-our-ev-50-amp-charger/HA-1214501881" class="class="static-page-link"">Ron &amp; Orline&#39;s Home, park at the door &amp; use our EV 50 amp charger</a> <a href="/property/pioneer-park-cottage-2-br-2-ba-downtown-historic-bardstown/HA-3211508350" class="class="static-page-link"">Pioneer Park Cottage, 2 BR/2 BA Downtown Historic Bardstown</a> <a href="/property/luxurious-suite-w-garden-on-court-square-downtown/HA-3211540452" class="class="static-page-link"">Luxurious Suite w/Garden on Court Square Downtown</a> <a href="/property/one-of-a-kind-cabin-in-the-woods-quiet-and-private-but-close-to-everything/HA-3212048721" class="class="static-page-link"">One of a kind cabin in the woods. Quiet and private but close to everything.</a> <a href="/property/a-room-off-broadway-a-prime-downtown-hideaway/HA-3213172203" class="class="static-page-link"">A Room Off Broadway, a prime downtown hideaway</a> <a href="/property/conveniently-located-in-downtown-bardstown/HA-3211080132" class="class="static-page-link"">Conveniently located in downtown Bardstown</a> <a href="/property/upscale-1-story-3-bd-2-ba-on-bourbon-trail-close-to-town-4-beds-3-xl-beds-q-s/HA-1217852256" class="class="static-page-link"">Upscale 1 STORY 3 Bd 2 Ba on BOURBON TRAIL Close to Town 4 Beds/3 XL Beds + Q/S</a>

How many vacation rentals have private pools in Boston?

There are 10 vacation rentals with private pools near Boston. Top-rated Theislandsadvisors homes that have access to a swimming pool include: <a href="/property/lux-lodge-3-mi-to-bardstown-spkez-hot-tub-game-rm/HA-3214878858" class="class="static-page-link"">Lux lodge~3 Mi to Bardstown~SpkEZ~Hot Tub~Game Rm</a> <a href="/property/fairfield-inn-suites-bardstown/BC-6457748" class="class="static-page-link"">Fairfield Inn &amp; Suites Bardstown</a> <a href="/property/farmhouse-only-10-minutes-from-jim-beam-distillery-and-bernheim-forest/HA-3213568868" class="class="static-page-link"">Farmhouse only 10 minutes from Jim Beam Distillery and Bernheim Forest!</a> <a href="/property/springhill-suites-by-marriott-elizabethtown/BC-4531310" class="class="static-page-link"">SpringHill Suites by Marriott Elizabethtown</a>

Which vacation homes in Boston are best for families?

If you are looking for a family-friendly vacation home in Boston, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Boston: <a href="/property/new-bourbon-on-the-square-downtown-rustic-loft/HA-3213078660" class="class="static-page-link"">NEW “Bourbon on the Square” Downtown Rustic Loft</a> <a href="/property/the-hutch/BC-14421210" class="class="static-page-link"">The Hutch</a> <a href="/property/jailer-s-inn/EP-27530196" class="class="static-page-link"">Jailer&#39;s Inn</a>

How many vacation rentals are available in Boston?

Currently, the total number of properties listed in 2026 is over 259 in the Boston area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Boston.