Search Southeast Massachusetts Cottage Accommodations

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Cottages in Southeast Massachusetts

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (144)
"We spent about a month in this absolutely wonderful home on Nantucket. When we arrived, it was clear the house has been professionally cleaned and was spotless. The kitchen is great for cooking for meals in. The tv room has a ton of natural light & was a great place to hang out as a family. There are 2 bedrooms, one on main floor which is easily accessible and 1 in the loft which is a steep staircase (fine for us as we have no mobility issues but bear this in mind). The little patio on the side...
Renovated Cottage off Main Street- Great Location

Hear the sound of the surf

2.0 star property
Hear the sound of the surf

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

9.6 out of 10, Exceptional, (100)
"A very comfortable few days on the mid-Cape. Great location, great little cottage. Quiet, private, clean. I'd do it again!"
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Peaceful waterfront cottage with furnished deck, beautiful view, firepit

7.2 out of 10, Good, (20)
"Nice little house on the lake. We enjoyed it. "
Peaceful waterfront cottage with furnished deck, beautiful view, firepit

Cozy beachfront cottage at Chases Ocean Grove

9.8 out of 10, Exceptional, (24)
"Enjoyed coffee on the enclosed porch overlooking ocean. Great communication with owner. Bathroom nicely done. Very clean, cute, well setup for a cottage. "
Cozy beachfront cottage at Chases Ocean Grove

2 Bedrooms + Loft - Sleeps 6 in Beds but max 4 adults- 5 Blocks to Town

10.0 out of 10, Exceptional, (96)
"Clean, cozy, well-located, it's a great spot for folks who want to stay together and have separate space at the same time. The adjoining unit makes this possible and unique in that way. "
2 Bedrooms + Loft - Sleeps 6 in Beds but max 4 adults- 5 Blocks to Town

LUXURIOUS Cottage with Breathtaking Harbor Views

10.0 out of 10, Exceptional, (139)
"Clean, comfy beds, and a fabulous location! Easy walk to town and other locations. "
LUXURIOUS Cottage with Breathtaking Harbor Views

Chappy cottage with private beach

10.0 out of 10, Exceptional, (14)
"This cottage was the perfect little getaway for our family to base our first visit on Chappy. We loved being able to walk to the beach and appreciated the cleanliness of the cottage as well as its charm. "
Chappy cottage with private beach

Quiet Plymouth Cottage on Great South Pond!

10.0 out of 10, Exceptional, (12)
"The perfect getaway spot! Tucked away on a pond hidden in the thick woods of Plymouth, this charming cottage was perfect for a weekend getaway! The pictures don't do their justice of how gorgeous this place is! The best is watching the sun set every evening during our stay! Gas, food, restaurants and stores are only a couple of minutes away. As well, Plymouth is only 15 minutes away! There is plenty to do in the area! But for a couples getaway, it was perfect for us to venture or stay in! Make...
Quiet Plymouth Cottage on Great South Pond!

Cozy Chatham Cottage walk to Hardings ⛱️ , Restaurants & downtown.

10.0 out of 10, Exceptional, (12)
"We greatly appreciate our hosts work with this cozy cottage. Indoor outdoor space was great for our family. Outdoor shower was a great bonus. Easy breeze into town or to Ridgevale Beach where our kids chased crabs for hours. Many thanks!"
Cozy Chatham Cottage walk to Hardings ⛱️ , Restaurants & downtown.

Free standing 1940s Artists Cottage East End near Commercial St. Parking! A/C!

9.6 out of 10, Exceptional, (10)
"Great place to stay, with parking. Couldn't have asked for better..."
Free standing 1940s Artists Cottage East End near Commercial St. Parking! A/C!

Oceanside 2 - SD335

9.6 out of 10, Exceptional, (13)
"House is set behind a dune. dune is a little steep, especially climbing back up. Kind of tough for the elderly. Set up of the house was good for 2 seniors. Many restaurants close by. Quiet area."
Oceanside 2 - SD335

2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town

10.0 out of 10, Exceptional, (86)
"Perfect set up for families traveling together. "
2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town

Oceanfront Cape Cod Gem w/ Balcony, Pets Welcome

9.2 out of 10, Wonderful, (57)
"We had a wounderful long weekend. "
Oceanfront Cape Cod Gem w/ Balcony, Pets Welcome

Lovely Cape Cottage 2 bedroom with private beach and central air.

10.0 out of 10, Exceptional, (44)
"Such a cute and comfortable place. We enjoyed the neighborhood and the beach down the street. Owner was really responsive if we needed anything "
Lovely Cape Cottage 2 bedroom with private beach and central air.

Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!

10.0 out of 10, Exceptional, (112)
"Quaint cottage, good location Perfect for 2 people "
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!

Lovely oceanfront cottage with deck, grill, & panoramic views

9.0 out of 10, Wonderful, (85)
"Fantastic view, cant say enough about sunrise and sunset. Nice away from it all spot close enough to places to go fora really good balance. The road in isa back road on the cape going any faster than 5mph will rattle you around but totally worth the slow roll in. "
Lovely oceanfront cottage with deck, grill, & panoramic views

Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

10.0 out of 10, Exceptional, (258)
"It was wonderful for two people! The property is close to beach, downtown and the free public buses. The property was clean, well equipped and easy to navigate. Loved our stay, and look forward to a return trip. Cudos to VRBO owner!"
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

Exquisite Oceanfont Cottage at Madaket Beach!

10.0 out of 10, Exceptional, (12)
"Fantastic property well aportioned and great communication. Would highly recommend"
Exquisite Oceanfont Cottage at Madaket Beach!

Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything

9.8 out of 10, Exceptional, (142)
"This was our second time staying at this property. It is in a great location and has many modern amenities. The beds are very comfortable with very nice linens. It is beautifully decorated and has everything you could want. Communication with property management was very good. "
Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything
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.
Don't see what you're looking for?
See all available properties in Southeast Massachusetts
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Southeast Massachusetts

Courtyard Resort

3.0 star property
8.6 out of 10, Excellent, (45)
"Great for short or extended stay. "
The price is AU$131
includes taxes & fees
7 Jan - 8 Jan
Courtyard Resort

Sandcastle Resort and Club

3.0 star property
7.4 out of 10, Good, (1015)
"Nice location, friendly staff, kitchenette had everything "
Sandcastle Resort and Club

Oceanside 2 - SD335

9.6 out of 10, Exceptional, (13)
"House is set behind a dune. dune is a little steep, especially climbing back up. Kind of tough for the elderly. Set up of the house was good for 2 seniors. Many restaurants close by. Quiet area."
Oceanside 2 - SD335
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.

Frequently asked questions

How much do cottages in Southeast Massachusetts cost?
You’ll pay between and per night for cottages in Southeast Massachusetts. No matter your budget, a wonderful stay is only a click away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Southeast Massachusetts?
Southeast Massachusetts has 129 cottages on offer. Enter your destination and travel dates and book your perfect trip today.
What is there to do in Southeast Massachusetts near my cottage?
Whether you’re interested in arts, culture, shopping or dining, Southeast Massachusetts promises something for everyone! The well-known city of Plymouth has loads of things to do and see, including Plimoth Patuxet Museums, Mayflower II and Plymouth Long Beach. If you’re holidaying in Hyannis, Cape Codder Water Park, Cape Cod Inflatable Park and John F. Kennedy Hyannis Museum shouldn’t be missed.