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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Guest Houses in Southeast Massachusetts and around

Our top choices for Southeast Massachusetts guest houses

Brass Key Guesthouse - Adults Only
Terrace/patio

Brass Key Guesthouse - Adults Only

4.0 star property
9.6 out of 10, Exceptional, (406)
"The Brass Key is always a delightful stay."
Brass Key Guesthouse - Adults Only
Mercury Hotel Provincetown
Deluxe Room

Mercury Hotel Provincetown

3.0 star property
9.0 out of 10, Wonderful, (437)
"Great place to stay. Walkable to everything in P Town "
Mercury Hotel Provincetown
Anchor Inn Beach House
Exterior

Anchor Inn Beach House

3.5 star property
9.2 out of 10, Wonderful, (410)
"Rooms and view were awesome!"
Anchor Inn Beach House
Sea Breeze Inn
Exterior

Sea Breeze Inn

2.5 star property
7.8 out of 10, Good, (181)
"Nice place to stay "
The price is €79
includes taxes & fees
16 Sept - 17 Sept
Sea Breeze Inn
The Lightkeepers Inn
Exterior

The Lightkeepers Inn

3.0 star property
9.6 out of 10, Exceptional, (193)
"Great location! "
The Lightkeepers Inn
The Bradford
Exterior

The Bradford

2.5 star property
9.4 out of 10, Exceptional, (193)
"Nice place"
The price is €226
includes taxes & fees
2 Sept - 3 Sept
The Bradford
Crew's Quarters Boarding House Caters to Men
Men's 1 double bed, Shared Bathroom

Crew's Quarters Boarding House Caters to Men

2.0 star property
9.4 out of 10, Exceptional, (66)
"The staff was very kind and helpful. Fun location!"
The price is €243
includes taxes & fees
2 Sept - 3 Sept
Crew's Quarters Boarding House Caters to Men
Languedoc Inn & 3 Hussey St Guest House
Exterior

Languedoc Inn & 3 Hussey St Guest House

2.5 star property
8.0 out of 10, Very good, (130)
"Hotel is old and terrible bathroom with noisy ventilation. You can hear your neighbours every movement. There is no door men or staff who can help with luggage. No breakfast including but it’s said on the Expedia that breakfast will be provided. I don’t recommend to stay there for this amount of money it’s not worth. "
Languedoc Inn & 3 Hussey St Guest House
Dyer's Beach House
Condo, 3 Bedrooms (Waterfront Condo 3 bedrooms) | Beach/ocean view

Dyer's Beach House

4.0 star property
9.8 out of 10, Exceptional, (67)
"Terrific location and waterfront views!"
Dyer's Beach House
Whaler's Inn
Traditional Room, 2 Single Beds, Non Smoking, Shared Bathroom

Whaler's Inn

3.0 star property
10.0 out of 10, Exceptional, (31)
"I would go again."
The price is €403
includes taxes & fees
26 Aug - 27 Aug
Whaler's Inn
Winstead Inn
Seasonal outdoor pool, pool umbrellas, pool loungers

Winstead Inn

4.0 star property
9.4 out of 10, Exceptional, (119)
"A wonderful property with a beautiful and quiet pool area and easy private beach access through its sister property."
The price is €147
includes taxes & fees
2 Sept - 3 Sept
Winstead Inn
By the Sea Guests Bed & Breakfast & Suites
Outdoor wedding area

By the Sea Guests Bed & Breakfast & Suites

3.5 star property
9.4 out of 10, Exceptional, (175)
"The location was awesome. Right on the beach. Room was clean and bathroom was clean good shower and water pressure. Breakfast was delicious and staff super friendly and polite."
The price is €186
includes taxes & fees
4 Sept - 5 Sept
By the Sea Guests Bed & Breakfast & Suites
The Seagrove Suites & Guest Rooms
Sun-loungers, beach umbrellas, beach towels

The Seagrove Suites & Guest Rooms

3.0 star property
9.2 out of 10, Wonderful, (125)
"The rooms were clean and spacious. Our little kitchen had everything we needed. The rooms are tucked away from the main road, so peaceful at night. The pool was clean and the water were warm. The owners were kind and accommodating and immediately available via txt"
The Seagrove Suites & Guest Rooms
Woods Hole Passage Inn
Property grounds

Woods Hole Passage Inn

3.0 star property
9.6 out of 10, Exceptional, (61)
"Incredibly friendly hosts and excellent breakfast! "
Woods Hole Passage Inn
The Rugosa Guest House
Lobby

The Rugosa Guest House

3.0 star property
8.8 out of 10, Excellent, (120)
"Wonderful guest house, room and property were lovely and excellent hospitality. Would definitely recommend and would plan a return visit! "
The Rugosa Guest House
All Seasons Resort
Indoor pool, outdoor pool

All Seasons Resort

9.0 out of 10, Wonderful, (50)
"This was a great experience. The owner has check in very organized and easy to understand. Probably the best place for the money I’ve ever stayed."
The price is €151
includes taxes & fees
1 Sept - 2 Sept
All Seasons Resort
The Chestnut House
Hallway

The Chestnut House

3.0 star property
9.4 out of 10, Exceptional, (191)
"Nice place for a family vacation on the island"
The price is €394
includes taxes & fees
15 Sept - 16 Sept
The Chestnut House
Madison Inn
Exterior

Madison Inn

2.5 star property
9.8 out of 10, Exceptional, (77)
"Great location! Very clean rooms and friendly staff."
Madison Inn
Charming guest house set on horse farm, walk to downtown Edgartown
Dining

Charming guest house set on horse farm, walk to downtown Edgartown

10.0 out of 10, Exceptional, (19)
"Great place with a wonderful owner. We hope to be back!"
Charming guest house set on horse farm, walk to downtown Edgartown
Brasswood Inn
Superior Room, 1 Queen Bed | Terrace/patio

Brasswood Inn

3.5 star property
9.6 out of 10, Exceptional, (125)
"Loved everything about our stay."
Brasswood Inn
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.
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Top Southeast Massachusetts Hotel Reviews

Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"We had a great 5 night stay . Bay view room great access to pool and kitchen below. The included breakfast worked out great . Our room service was great we will definitely stay again . "
Finnegan 5-night trip
Posted 11 hours ago
Bayside Resort Hotel