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Search Vacation Homes in Eastern Massachusetts

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Fishtales, a Bright, Clean and Comfortable in Town Home!
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This family-friendly Nantucket vacation home is located near the beach, within a 5-minute walk of Historic Mitchell House, Greater Light Garden, and Hadwen House. ...

5/5Exceptional! (14 reviews)
Small family gathering for Christmas, wonderful!

"We always enjoy staying at Fishtales, which is a lovely, livable home less than a half mile from downtown. The property manager is always easy to communicate with, and on this trip we had one small plumbing inconvenience that we were able to work around. Despite covid and its restrictions we were ..."…"

Reviewed on Jan 2, 2021

Fishtales, a Bright, Clean and Comfortable in Town Home!
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
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This family-friendly Chatham vacation home is located on the waterfront, within a 15-minute walk of Chatham Lighthouse Beach, Chatham Seaside Links, and Monomoy ...

4.9/5Exceptional! (40 reviews)
Beautiful and spacious house with the perfect location

"We had 10 adults and plenty of space at this house. The owners were on top of communication and check in was easy. Would love to stay at this location again."…"

Reviewed on Feb 22, 2021

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
16 Riverview Drive - Three Bedroom Home
3.5 out of 5
16 Riverview Drive, Chatham, MA
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Situated in Chatham, this vacation home is within 3 mi (5 km) of Caleb Nickerson House, Chatham Chamber of Commerce, and Ridgevale Beach. Cockle Cove Beach and ...

16 Riverview Drive - Three Bedroom Home
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26 Whiteleys Way - Four Bedroom House
3 out of 5
26 Whiteleys Way, Chatham, MA
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Situated in Chatham, this vacation home is within 3 mi (5 km) of Hardings Beach, Chatham Chamber of Commerce, and Ridgevale Beach. Cockle Cove Beach and Monomoy ...

26 Whiteleys Way - Four Bedroom House
Newly Updated Home on Simmons Pond w/ Private Dock & Porch - Near Downtown
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This family-friendly Hyannis vacation home is within 1 mi (2 km) of Keyes Beach, Keyes Memorial Beach, and Hyannis Port Beach. Hyannis Harbor and Cape Codder ...

4.2/5Very Good! (6 reviews)
Almost perfect

"Aside from a few minor issues, the property was amazing. I would have loved to have either an early check-in or a late check-out. The site made it seem like one was very possible but we weren't accommodated with either. Because of this, I would recommend booking an extra day."…"

Reviewed on Aug 31, 2020

Newly Updated Home on Simmons Pond w/ Private Dock & Porch - Near Downtown
NANTUCKET IN TOWN sleeps up to 8 - New Home Highest Quality! Convenient LUXURY
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Located in Nantucket Town, this vacation home is within a 10-minute walk of Old Mill, Nantucket Lightship Basket Museum, and Hadwen House. Historic Mitchell ...

5/5Exceptional! (14 reviews)
Very nice and cozy place

"Very nice and cozy place"…"

Reviewed on Sep 14, 2020

NANTUCKET IN TOWN sleeps up to 8 - New Home Highest Quality! Convenient LUXURY
35 Cory Lane - Three Bedroom House
3.5 out of 5
35 Cory Lane, Chatham, MA
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Situated in Chatham, this vacation home is within a 15-minute walk of Ridgevale Beach and Cockle Cove Beach. Chatham Chamber of Commerce and Forest Beach are ...

35 Cory Lane - Three Bedroom House
New Listing! Downtown Studio w/ Full Kitchen - Walk to Bay and Shops!
The price is $92 per night from Mar 11 to Mar 12

Located in the heart of Provincetown, this historic vacation home is steps from Provincetown Town Hall, Ryder Street Beach, and Town Beaches. Meetinghouse Theatre ...

3.7/5Good! (3 reviews)
Just what you need!

"This apartment was quaint and nothing more than you needed!"…"

Reviewed on Nov 10, 2020

New Listing! Downtown Studio w/ Full Kitchen - Walk to Bay and Shops!
154 Old Harbor Road - Three Bedroom House
3.5 out of 5
154 Old Harbor Road, Chatham, MA
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Situated in Chatham, this vacation home is within a 5-minute walk of Chatham Railroad Museum and Veterans Field. Chatham Seaside Links and Monomoy Theatre are ...

154 Old Harbor Road - Three Bedroom House
2 Bedroom Apartment in Boston by TD Garden!
The price is $400 per night from Mar 6 to Mar 7

Located in West End, this romantic vacation home is within a 10-minute walk of TD Garden and Boston Harbor. The Freedom Trail and Massachusetts General Hospital ...

2 Bedroom Apartment in Boston by TD Garden!
28 Capri Lane - Two Bedroom House
3 out of 5
28 Capri Lane, Chatham, MA
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Situated in Chatham, this vacation home is within 1 mi (2 km) of Chatham Windmill, Monomoy Theatre, and Chatham Railroad Museum. Veterans Field and Chatham Seaside ...

28 Capri Lane - Two Bedroom House
Perfect Location in Central Square
The price is $199 per night from Mar 15 to Mar 16

Located in Inman Square, this vacation home is within 1 mi (2 km) of MIT Museum, Massachusetts Institute of Technology (MIT), and Harvard University. Harvard ...

5/5Exceptional! (1 review)
Cambridge Christmas 2020

"Great location and comfy home. The family enjoyed the location and enjoyed a great Christmas on the east coast. Easy to work with owners, and fast communication stream. Home cooked meals were easy to do during these times and the lack of dine in restaurants. Local take out available within walking ..."…"

Reviewed on Dec 30, 2020

Perfect Location in Central Square
Great Location Walk TO Beach DOG Friendly
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This family-friendly West Yarmouth vacation home is within 1 mi (2 km) of Putter's Paradise Miniature Golf and Hyannis Harbor. Wild Animal Lagoon and Lewis Bay ...

4.9/5Exceptional! (23 reviews)
Beautiful, clean and well maintained

"Perfect for enjoying your vacation relaxing on the wrap around porch with a glass of wine or cold tea with plenty of amenities provided. The owner's really thought of everything you could need to enjoy your stay. Very comfortable, clean and located in a nice neighborhood."…"

Reviewed on Aug 24, 2020

Great Location Walk TO Beach DOG Friendly
Lavish : Amazing Locale Near Dining & Beach 1 Bedroom Condo
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Situated in Chatham, this vacation home is within a 15-minute walk of Chatham Windmill, Monomoy Theatre, and Chatham Seaside Links. Chatham Railroad Museum and ...

Lavish : Amazing Locale Near Dining & Beach 1 Bedroom Condo
76 Indian Hill Road North - Three Bedroom House
3.5 out of 5
76 Indian Hill Road North, Chatham, MA
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Situated in Chatham, this vacation home is within 3 mi (5 km) of Chatham Drama Guild, Chatham Chamber of Commerce, and Caleb Nickerson House. Monomoy Theatre ...

76 Indian Hill Road North - Three Bedroom House
Gorgeous home in town! 3 br,/3ba ,screened porch- 3 levels of living & parkingx2
The price is $664 per night from Mar 6 to Mar 7

Located in Nantucket Town, this family-friendly Nantucket vacation home is within a 10-minute walk of Historic Mitchell House, Loines Observatory, and Greater ...

5/5Exceptional! (9 reviews)
Perfect weekend getaway

"Everything about this house was perfect; the layout was open, yet provided enough privacy, the screened in back porch was a dream, and the front porch was so private and our 2 year old enjoyed many hours playing on the deck. We loved walking in to town for dinner, ice cream and shopping. The house ..."…"

Reviewed on Oct 6, 2019

Gorgeous home in town! 3 br,/3ba ,screened porch- 3 levels of living & parkingx2
Harvard House Boutique Conference Center and Guest Quarters
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Located in Waltham, this family-friendly vacation home is 2.6 mi (4.3 km) from Brandeis University, and within 9 mi (15 km) of MIT Museum and Boston College. ...

4.8/5Exceptional! (23 reviews)
Perfect Spot for a Small Winter Wedding!

"This spot was great for our outdoor winter micro-wedding - stunning setting for photography with the woods on the property and the house itself is gorgeous. The house had enough space for our family to stay there and be comfortable, and we appreciated that our wedding venue could double as family ..."…"

Reviewed on Feb 5, 2021

Harvard House Boutique Conference Center and Guest Quarters
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach
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Situated by the ocean, this vacation home is within a 15-minute walk of Chatham Windmill, Monomoy Theatre, and Chatham Seaside Links. Chatham Railroad Museum ...

4.6/5Exceptional! (8 reviews)
Chatham Honeymoon

"Friends had told us we would have a great honeymoon in Chatham. They were right. A wonderful place to start our adventure as husband and wife."…"

Reviewed on Nov 10, 2020

New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach
New Luxury House,  150 yards to Nantucket Beaches, AC, WiFi, Linens,Towels....
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Situated by the ocean, this vacation home is 0.2 mi (0.3 km) from Keyes Memorial Beach and within 3 mi (5 km) of Hyannis Harbor and Cape Codder Water Park. Keyes ...

5/5Exceptional! (57 reviews)
Comfortable and convenient

"Was perfect for our girls weekend."…"

Reviewed on Feb 24, 2021

New Luxury House, 150 yards to Nantucket Beaches, AC, WiFi, Linens,Towels....
Historic Brick Federal Period Mansion on Fabled Chestnut Street, Salem
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Located in the center of Salem, this family-friendly vacation home is within a 10-minute walk of Phillips House and Witch House. Salem Witch Museum and Salem ...

4.9/5Exceptional! (24 reviews)
Wonderful Family Stay

"My family just returned from a four night Salem. What a wonderful home and great location for walking to all the museums and restaurants. Richard was a great host and very helpful. Looking forward to returning during this beautiful time of year."…"

Reviewed on Oct 28, 2020

Historic Brick Federal Period Mansion on Fabled Chestnut Street, Salem
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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.

Other property types in Eastern Massachusetts

citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
The price is $99 per night from Mar 7 to Mar 8
4.6/5Wonderful! (1,422 reviews)

"Very clean, and strict with Covid regulations which made you feel safer. Parking.... had to pay at the garage and you don’t get to come in an out, so plan ahead if you’re traveling. It’s expensive"…"

Reviewed on Feb 17, 2021

citizenM Boston North Station
Loews Boston Hotel

Loews Boston Hotel

4 out of 5
154 Berkeley Street, Boston, MA
The price is $129 per night from Mar 6 to Mar 7
4.6/5Wonderful! (985 reviews)

"El trato del personal fue excelente, siempre muy amables y atentos"…"

Reviewed on Feb 16, 2021

Loews Boston Hotel
Boston Park Plaza

Boston Park Plaza

4 out of 5
50 Park Plaza at Arlington Street, Boston, MA
The price is $125 per night from Mar 7 to Mar 8
4.1/5Very Good! (5,049 reviews)

"I didnt like tge fact that restaurant was closed. It was available for take out. The room were very nice. The bed was very comfortable."…"

Reviewed on Feb 23, 2021

Boston Park Plaza
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.

Booking Tips to Find the Best Eastern Massachusetts Vacation Homes


How much does it cost to rent a vacation home in Eastern Massachusetts?

You can find incredible Eastern Massachusetts vacation homes for all types of budgets: between $92 and $664 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Eastern Massachusetts?

If you are looking for a great deal on your vacation home in Eastern Massachusetts, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Eastern Massachusetts?

There are 253 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Eastern Massachusetts?

Begin by entering your trip dates to see what type of Eastern Massachusetts rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Eastern Massachusetts?

Booking Eastern Massachusetts vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Eastern Massachusetts rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Eastern Massachusetts along with your vacation property, into a Eastern Massachusetts vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

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