Guesthouse vacation rentals in Boston

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Boston

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

Guest favorite
Guesthouse in Boston
The Red Door Carriage House
The Red Door Carriage house is a historic 90 year-old structure that was the carriage house for the original farmhouse (our home) on the property. Located in beautiful West Roxbury Mass., the unit is 3 miles from Fenway (Red Sox), Longwood Medical Center (all of the major hospitals) and 2 miles from Boston College. A 5 minute walk to the West Roxbury commuter rail station (10 minutes to South Station) and all bus lines into Boston, this apartment is a spectacular private and tranquil retreat.
Jul 5 – 12
$280 per night
4.99 out of 5 average rating, 225 reviews
Guest favorite
Guesthouse in North Andover
Spacious Studio Guesthouse at Winery w/ Tasting
*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!
Aug 7 – 14
$525 per night
4.97 out of 5 average rating, 177 reviews
Guest favorite
Guesthouse in Framingham
Private guest house on beautiful country road
Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.
Oct 4 – 11
$90 per night
4.97 out of 5 average rating, 189 reviews

Popular amenities for Boston guesthouse rentals

Family-friendly guest house rentals

Superhost
Guesthouse in Shrewsbury
A Comfy Hilltop Home
Jun 28 – Jul 5
$95 per night
4.71 out of 5 average rating, 194 reviews
Guest favorite
Guesthouse in Boston
Airy new apt for 4-6. Near subway. Free parking.
Dec 3 – 10
$220 per night
4.89 out of 5 average rating, 28 reviews
Guesthouse in Boston
Boston’s Luxury Cellar Apartment, Comfy & Cozy
Feb 18 – 25
$110 per night
4.78 out of 5 average rating, 116 reviews
Guest favorite
Guesthouse in Salem
Spacious 3 bedroom Suite Sleeps 6-8. 4 Beds
Aug 26 – Sep 2
$318 per night
4.97 out of 5 average rating, 64 reviews
Guest favorite
Guesthouse in Somerville
Private room w/ private bath - single family house
May 2 – 9
$126 per night
4.94 out of 5 average rating, 186 reviews

Guest house rentals with a patio

Guest favorite
Guesthouse in Beverly
Adorable 1-bedroom carriage house
Nov 16 – 23
$158 per night
4.98 out of 5 average rating, 108 reviews
Guest favorite
Guesthouse in Melrose
Jimmy & Donny's AirBnB
Jan 2 – 9
$110 per night
4.96 out of 5 average rating, 55 reviews
Superhost
Guesthouse in Braintree
The Pool House
Apr 20 – 27
$114 per night
4.71 out of 5 average rating, 17 reviews
Guest favorite
Guesthouse in Marblehead
Debby's Guesthouse - 2-Bedroom Getaway
Jun 3 – 10
$180 per night
5.0 out of 5 average rating, 18 reviews
Guesthouse in Winthrop
The Strand on the Beach
Dec 15 – 22
$200 per night
4.81 out of 5 average rating, 43 reviews
Guesthouse in Malden
Northern Suburb
Nov 23 – 30
$221 per night
4.81 out of 5 average rating, 43 reviews

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Westford
Detached Waterfront Guest House
Aug 28 – Sep 4
$115 per night
4.97 out of 5 average rating, 79 reviews
Superhost
Guesthouse in Lexington
Unique Loft/ Studio Guesthouse (super convenient)
Sep 4 – 11
$99 per night
4.71 out of 5 average rating, 180 reviews
Guest favorite
Guesthouse in Newton
Sunny 1BR w views, close to BC and Boston
Mar 15 – 22
$374 per night
4.99 out of 5 average rating, 68 reviews
Superhost
Guesthouse in Cambridge
Beautiful Cambridgeport Apartment (Central Square)
Feb 9 – 16
$271 per night
4.89 out of 5 average rating, 9 reviews
Guest favorite
Guesthouse in Melrose
Modern, Cute 1.5 BR Carriage House North of Boston
Aug 15 – 22
$184 per night
5.0 out of 5 average rating, 53 reviews
Guest favorite
Guesthouse in Cohasset
Lovely 1 Bedroom Guest House. Downtown Cohasset
Apr 12 – 19
$160 per night
4.98 out of 5 average rating, 100 reviews
Guest favorite
Guesthouse in Saugus
Private apartment 1 bed 1 bath a day bed Trundle
Jul 1 – 8
$167 per night
5.0 out of 5 average rating, 45 reviews
Superhost
Guesthouse in Framingham
Enchanted Cottage on 5 Acres
Mar 19 – 26
$185 per night
New place to stay
Guesthouse in Shrewsbury
Lovely & Spacious 2 BR (W/KING/QUEEN beds) 2 BTH.
Mar 19 – 26
$124 per night
4.69 out of 5 average rating, 35 reviews
Guest favorite
Guesthouse in Westford
Charming 1880 Historic Carriage House
Mar 19 – 26
$250 per night
4.99 out of 5 average rating, 95 reviews
Guesthouse in Newton
Deluxe 2-bedroom 2-story with gas fireplace house
Nov 25 – Dec 2
$347 per night
4.56 out of 5 average rating, 9 reviews
Superhost
Guesthouse in Billerica
The Pool House at The Acropolis
Mar 7 – 14
$96 per night
4.97 out of 5 average rating, 92 reviews

Quick stats about guesthouse rentals in Boston

Total rentals

20 properties

Local attractions

Fenway Park, Boston Common, and TD Garden

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Total number of reviews

2.4K reviews

Destinations to explore