A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.

Search Guest Houses in Eastern Massachusetts

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

Our top choices for Eastern Massachusetts guest houses

A spacious living room with a wooden ceiling, a sofa, a coffee table, and a bookshelf.

1. Mercury Hotel Provincetown

Mercury Hotel Provincetown
3.0 star property
Provincetown
9.2 out of 10, Wonderful, (567 reviews)
"Cool little property with a great vibe and fantastic location. Rooms are small but clean, if a little dated. Great common areas. Roof top deck was closed off while we were there for repairs? Definitely would stay here again and recommend it to anyone looking for a great location and reasonably priced property to spend a weekend in Provincetown."
United States
Steven
The price is ￥12,954
￥16,307 total
includes taxes & fees
Nov 2 - Nov 3
Mercury Hotel Provincetown
A wooden house with a porch, a Christmas tree, and string lights.

2. Nantucket Guest House

Nantucket Guest House
3.0 star property
Nantucket
9.8 out of 10, Exceptional, (68 reviews)
"Great staff and accommodations for our visit."
United States
Steve
The price is ￥15,644
￥29,830 total
includes taxes & fees
Oct 19 - Oct 20
Nantucket Guest House
A large, multi-story house with a swimming pool, outdoor seating, and a balcony.

3. Brass Key Guesthouse - Adults Only

Brass Key Guesthouse - Adults Only
4.0 star property
Provincetown
9.6 out of 10, Exceptional, (574 reviews)
"It was amazing, staff were great!"
United States
Harold
The price is ￥27,392
￥31,351 total
includes taxes & fees
Nov 2 - Nov 3
Brass Key Guesthouse - Adults Only
A cozy living room with a fireplace, bookshelves, a dining area, and a staircase.

4. Madison Inn

Madison Inn
2.5 star property
Oak Bluffs
9.8 out of 10, Exceptional, (84 reviews)
"Good location, friendly staff. More breakfast/drink options would have been good."
United States
Melissa
The price is ￥31,983
￥36,605 total
includes taxes & fees
Nov 4 - Nov 5
Madison Inn
A cozy living room with a leather sofa, a round coffee table with books and a disco ball, a fireplace, and a bookshelf.

5. The Ipswich Inn

The Ipswich Inn
2.0 star property
Ipswich
8.8 out of 10, Excellent, (52 reviews)
"Quiet and cute inn"
United States
Donna
The price is ￥19,376
￥21,256 total
includes taxes & fees
Nov 4 - Nov 5
The Ipswich Inn
A modern hotel room with a kitchenette, a dining area, and a bedroom with a bed and a window.

6. Cutwater Inn & Suites

Cutwater Inn & Suites
3.5 star property
Newburyport
8.8 out of 10, Excellent, (35 reviews)
"These rooms were small but they were so nice and well decorated and the bathrooms were great with all new decor. Great shower! Very clean and efficient."
United States
Lisa
The price is ￥21,460
￥25,353 total
includes taxes & fees
Nov 3 - Nov 4
Cutwater Inn & Suites
A bedroom with a floral-patterned sofa, a round rug, a dresser, and a television mounted on the wall.

7. Sea Breeze Inn

Sea Breeze Inn
2.5 star property
Hyannis
7.8 out of 10, Good, (222 reviews)
"The inn was cozy and clean Directions on the phone to get in the room. Of course I was there off season , but great location. Short walk to the beach. Just lovely, and wonderful for a solo traveler."
United States
Ann
The price is ￥12,484
￥14,287 total
includes taxes & fees
Nov 1 - Nov 2
Sea Breeze Inn
A room with wooden walls, a leather chair, a small table with a lamp, and a clock on the wall.

8. Crew's Quarters Boarding House Caters to Men

Crew's Quarters Boarding House Caters to Men
2.0 star property
Provincetown
9.6 out of 10, Exceptional, (86 reviews)
"Enjoyed the property and my stay. Will return."
United States
Christopher
The price is ￥29,550
￥33,820 total
includes taxes & fees
Oct 23 - Oct 24
Crew's Quarters Boarding House Caters to Men
A two-story house with a well-lit front porch, a staircase leading to the entrance, and a garden with various plants and flowers.

9. Winstead Inn

Winstead Inn
4.0 star property
Harwich
9.4 out of 10, Exceptional, (158 reviews)
"Peaceful and beautiful property. Staff was wonderful."
United States
Karen
The price is ￥35,555
￥40,694 total
includes taxes & fees
Oct 21 - Oct 22
Winstead Inn
A kitchen with blue cabinets, a white refrigerator, a coffee maker, and a sink with a gold faucet.

10. The Lightkeepers Inn

The Lightkeepers Inn
3.0 star property
Edgartown
9.4 out of 10, Exceptional, (220 reviews)
"The lightkeepers in was perfect. Would definitely go back"
United States
Penny
The price is ￥33,263
￥37,155 total
includes taxes & fees
Oct 29 - Oct 30
The Lightkeepers Inn
A two-story house with a balcony and a porch.

11. Anchor Inn Beach House

Anchor Inn Beach House
3.5 star property
Provincetown
9.4 out of 10, Exceptional, (474 reviews)
"Perfect location, beautiful view"
United States
luisa
The price is ￥51,028
￥58,403 total
includes taxes & fees
Oct 19 - Oct 20
Anchor Inn Beach House
A house with a pond in front, surrounded by autumn-colored trees.

12. The Inn on the Horse Farm

The Inn on the Horse Farm
3.0 star property
Sudbury
8.0 out of 10, Very good, (286 reviews)
"well maintained, beautiful Tv kept buffering-- that cannot happen no toilet or sink in room"
United States
Steven
The price is ￥25,861
￥28,887 total
includes taxes & fees
Nov 1 - Nov 2
The Inn on the Horse Farm
A bedroom with a bed, a desk, and a chair.

13. Tranquil House in Cambridge

Tranquil House in Cambridge
3.0 star property
Strawberry Hill
8.8 out of 10, Excellent, (187 reviews)
"Responsive owner, easy to find with maps, easy parking out front- very clean and efficient so so quiet!!"
United States
Lisa
The price is ￥23,219
￥26,575 total
includes taxes & fees
Oct 19 - Oct 20
Tranquil House in Cambridge
A neatly made bed with pillows and a rolled towel, a bedside table with a lamp, and a window with curtains.

14. The Bradford

The Bradford
2.5 star property
Provincetown
9.4 out of 10, Exceptional, (261 reviews)
"Great stay and friendly staff"
United States
Matthew
The price is ￥32,204
￥36,858 total
includes taxes & fees
Oct 19 - Oct 20
The Bradford
A bedroom with a bed, a red chair, a small table with a book, a potted plant, and a staircase leading to an outdoor area.

15. Cambridge Common House

Cambridge Common House
4.0 star property
West Cambridge
10.0 out of 10, Exceptional, (51 reviews)
"Beautifully designed rooms, impeccable service, and really great location. Loved Cambridge Common House - I think the best hotel option in Harvard Square at the moment, and a really great addition to the area."
United Kingdom
Omolola
The price is ￥32,293
￥36,960 total
includes taxes & fees
Nov 1 - Nov 2
Cambridge Common House
A plate of French toast with bananas on a beach view.

16. By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites
3.5 star property
Dennis Port
9.2 out of 10, Wonderful, (249 reviews)
"Amazing stay. Great place right on the beach. Will be back."
United States
Jason
The price is ￥31,794
￥40,909 total
includes taxes & fees
Oct 23 - Oct 24
By the Sea Guests Bed & Breakfast & Suites
A bedroom with a large clawfoot bathtub, a four-poster bed, and a wooden ceiling.

17. Silsbee's by Daniels House

Silsbee's by Daniels House
4.0 star property
Salem
9.6 out of 10, Exceptional, (93 reviews)
"Very charming place to stay."
United States
Amy
The price is ￥46,918
￥52,407 total
includes taxes & fees
Nov 17 - Nov 18
Silsbee's by Daniels House
A historic brick building with a prominent 'Breckinridge Inn' sign, a stone staircase, and a large window.

18. Beacon Inn 1750

Beacon Inn 1750
3.0 star property
Brookline
7.6 out of 10, Good, (814 reviews)
"Excellent location, close to great food ,best bagels in Brookline (mamalehs), and superb tacos (bartaco), easy access to T."
United States
Sharon
The price is ￥20,513
￥22,913 total
includes taxes & fees
Nov 15 - Nov 16
Beacon Inn 1750
A large, two-story house with a central entrance, large windows, and a well-maintained lawn.

19. Chapter House

Chapter House
3.5 star property
Yarmouth Port
9.2 out of 10, Wonderful, (189 reviews)
"We got a room at the Chapter House last minute and it was absolutely perfect for a place to stay after the beach and dinner. The staff was super welcoming and thorough with check in well they gave us a tour. Would definitely stay again!"
United States
JULIE
The price is ￥47,307
￥54,144 total
includes taxes & fees
Oct 19 - Oct 20
Chapter House
A bedroom with a bed, a chair, a fireplace, and a television.

20. Beacon Inn 1087

Beacon Inn 1087
2.5 star property
Longwood
8.0 out of 10, Very good, (880 reviews)
"We had a very relaxed stay! Easy late check in and affordable parking."
United States
Julie
The price is ￥20,513
￥22,913 total
includes taxes & fees
Nov 15 - Nov 16
Beacon Inn 1087
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Eastern Massachusetts Hotel Reviews

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"Well maintained. Wish they had ac"
James 2-night trip
Posted 6 hours ago
The Midtown Hotel MOD Collection by Sonesta

Find out more about Eastern Massachusetts

Eastern Massachusetts Guest Houses information

Number of reviews
3,588
Accommodation
35 Guest Houses
Lowest Price
￥14,287
Highest Price
￥58,403

Explore a world of travel with Expedia