Book Guesthouses in Massachusetts

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

magnifying-glass.svgclose.svg
December 2025
Dec 2025
MonTueWedThuFriSatSun
Jan 2026
MonTueWedThuFriSatSun

Wednesday 31 December 2025 - Thursday 01 January 2026 (1 night)

calender.png
31 Dec 2025
Wednesday
calender.png
01 Jan 2026
Thursday
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

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

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

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

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

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
promotion

INVITE AND EARN REWARDS

Give US$25 and Get US$25 for referring friends!

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

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

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

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

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

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

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

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

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

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.