Book Guesthouses in Massachusetts

Find your next stay with 2,200,000+ Hotels, Homes, Apartments & Villas

magnifying-glass.svgclose.svg
March 2026
Mar 2026
MonTueWedThuFriSatSun
Apr 2026
MonTueWedThuFriSatSun

Tuesday 24 March 2026 - Wednesday 25 March 2026 (1 night)

calender.png
24 Mar 2026
Tuesday
calender.png
25 Mar 2026
Wednesday
people.png
2 Adults - 0 Child
1 room
Explore

Massachusetts

Find in some of the most popular cities in Massachusetts
Loading...

Massachusetts - 41 Guesthouses to stay

Find guesthouse deals in Massachusetts
See map view
best price
Best Price Guarantee

We guarantee we won't be beaten on price. If you find a cheaper hotel deal on another website after you book with us, we’ll refund the difference!

See the latest prices and deals by choosing your dates. Choose dates
Copley House

Copley House

239 W Newton St, Boston, USA - See map
Free WiFiParking availableConciergeAmenities

Excellent

892 Guest reviews

8.2
Cleanliness8.4/10
Service8.4/10
Comfort8.0/10
Condition7.8/10
Neighborhood9.8/10
Amenities7.4/10
Check Availability
Oasis Guest House

Oasis Guest House

22 Edgerly Road, Boston, USA - See map
Free WiFiParking availableConciergeAmenities

Wonderful

892 Guest reviews

9.2
Cleanliness9.4/10
Service9.4/10
Comfort8.6/10
Condition8.8/10
Neighborhood9.4/10
Amenities8.6/10
Check Availability
Bedrooms near Fenway & Downtown Boston

Bedrooms near Fenway & Downtown Boston

182 Heath St, Boston, USA - See map
Free WiFiParking availableConciergeAmenities

Poor

58 Guest reviews

3.6
Cleanliness4.0/10
Service3.8/10
Comfort4.0/10
Condition3.8/10
Amenities3.6/10
Check Availability
promotion

2% giveback on bookings

Create an account or login to unlock these rewards

Brass Key Guesthouse - Adults Only

Brass Key Guesthouse - Adults Only

67 Bradford St, Provincetown, USA - See map
Swimming PoolFree WiFiParking availableAmenities

Exceptional

141 Guest reviews

9.6
Cleanliness9.6/10
Service9.6/10
Comfort9.6/10
Condition9.6/10
Neighborhood9.4/10
Amenities9.6/10
Check Availability
Coolidge Corner Guest House

Coolidge Corner Guest House

17-19 Littell Road, Brookline, USA - See map
Free WiFiParking availableDining servicesAmenities

Excellent

289 Guest reviews

8.2
Cleanliness8.8/10
Service8.6/10
Comfort7.8/10
Condition7.8/10
location8.2/10
Neighborhood9.0/10
Amenities8.0/10
Check Availability
Moroccan Boutique Guest House

Moroccan Boutique Guest House

8 Salem Street, Boston, USA - See map
Free WiFiNon-smoking

Exceptional

60 Guest reviews

9.8
Cleanliness10/10
Service9.8/10
Comfort9.8/10
Condition9.6/10
location8.4/10
Neighborhood9.2/10
Amenities9.8/10
Check Availability
Crew's Quarters Boarding House Caters to Men

Crew's Quarters Boarding House Caters to Men

198 Commercial St, Provincetown, USA - See map
Free WiFiConciergeEntertainmentAmenities

Excellent

130 Guest reviews

8.2
Cleanliness8.4/10
Service8.8/10
Comfort7.4/10
Condition7.8/10
Neighborhood9.4/10
Amenities8.2/10
Check Availability
Beacon Inn 1750

Beacon Inn 1750

1750 Beacon Street, Brookline, USA - See map
Free WiFiParking availableConciergeAmenities

Good

523 Guest reviews

7.4
Cleanliness8.0/10
Service7.8/10
Comfort7.4/10
Condition7.2/10
location8.2/10
Neighborhood8.6/10
Value7.8/10
Amenities6.8/10
Check Availability
The Bradford

The Bradford

41 Bradford St, Provincetown, USA - See map
Free WiFiParking availableDining servicesAmenities

Wonderful

105 Guest reviews

9.0
Cleanliness9.4/10
Service9.2/10
Comfort8.8/10
Condition9.2/10
Neighborhood10/10
Amenities8.6/10
Check Availability
Mercury Hotel

Mercury Hotel

12 Winthrop St., Provincetown, USA - See map
Free WiFiParking availableConciergeAmenities

Excellent

278 Guest reviews

8.8
Cleanliness9.6/10
Service8.6/10
Comfort8.4/10
Condition9.2/10
location9.8/10
Neighborhood9.8/10
Quality8.8/10
Value8.4/10
Amenities8.6/10
Check Availability
Dyer's Beach House

Dyer's Beach House

173 Commercial Street, Provincetown, USA - See map
Free WiFiParking availableAirport transfersAmenities

Exceptional

51 Guest reviews

9.6
Cleanliness10/10
Service9.6/10
Comfort9.6/10
Condition9.8/10
Neighborhood10/10
Amenities9.6/10
Check Availability
Brasswood Inn

Brasswood Inn

174 Commercial Street, Provincetown, USA - See map
Free WiFiParking availableDining servicesAmenities

Exceptional

113 Guest reviews

9.4
Cleanliness9.4/10
Service9.6/10
Comfort9.2/10
Condition9.2/10
location10/10
Neighborhood9.8/10
Amenities9.4/10
Check Availability
Clarendon Square

Clarendon Square

198 West Brookline Street, Boston, USA - See map
Parking availableConciergeLaundryAmenities

Exceptional

101 Guest reviews

9.6
Cleanliness9.6/10
Service9.6/10
Comfort9.6/10
Condition9.8/10
Neighborhood9.6/10
Amenities9.2/10
Check Availability
Beacon Inn 1087

Beacon Inn 1087

1087 Beacon St, Brookline, USA - See map
Free WiFiParking availableConciergeAmenities

Very Good

534 Guest reviews

7.6
Cleanliness8.2/10
Service8.0/10
Comfort7.4/10
Condition7.4/10
location8.6/10
Neighborhood8.6/10
Value7.6/10
Amenities7.2/10
Check Availability
The Seagrove Suites & Guest Rooms

The Seagrove Suites & Guest Rooms

25 Seaview Rd, Eastham, USA - See map
Swimming PoolFree WiFiParking availableAmenities

Wonderful

94 Guest reviews

9.2
Cleanliness9.4/10
Service9.2/10
Comfort8.8/10
Condition9.0/10
location8.0/10
Neighborhood8.4/10
Amenities9.6/10
Check Availability
See all guesthouses in Massachusetts

Search by Holiday Style

Discover your ideal stay: explore pet-friendly homes, eco retreats, luxury accommodations, and more
Loading...

Continue Your Adventure

  • All regions in the USA
  • Flights to All Regions
  • Top Massachusetts Destinations
  • Hotels Near Airports
  • Explore More Hotels

Explore Our Travel Guides

  • Travel Planning
  • CRYPTO
  • Travel Destination
  • Accommodation Guides
  • Travel Trends
  • News

FAQs

      More Ways to Explore Massachusetts

      You might also like these destinations while on your trip

      Customer Reviews
      What our customers say

      Crypto-friendly Bookings

      Your money’s good here.

      We pride ourselves on being the leading crypto-native travel platform. Pay for your travel anywhere in the world seamlessly using 100+ cryptocurrencies or traditional payments.