Holiday Homes in Southeast Massachusetts

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Featured Holiday Homes in Southeast Massachusetts and around

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

10.0 out of 10, Exceptional, (159)
"Place was adorable perfect for what we needed. Perfect location, centralized for all your needs and wants"
The price is €330
includes taxes & fees
14 Aug - 15 Aug
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants

10.0 out of 10, Exceptional, (94)
"Loved our stay. Property is very clean and in a quiet neighborhood close to town and beaches. Host Bonnie was great. Would definitely rent again."
Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants

Hyannis Hideaway in Cape Cod

10.0 out of 10, Exceptional, (2)
"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "
The price is €734
includes taxes & fees
3 Sept - 4 Sept
Hyannis Hideaway in Cape Cod

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.0 out of 10, (22)
"There were times when the shower in the master bathroom only emitted cold water. The water spigot in the tubs would not turn completely off in bathroom in the hallway. I had trouble with the lockbox. Maybe add more specific directions. It would have been helpful to know that MV transit bus was available at the intersection of the street and County Road."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

8.2 out of 10, Very good, (36)
"Perfect for one or two people, was great for myself and my dog to stay."
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

Totally Renovated Central AC Dog Friendly Near Golf

9.6 out of 10, Exceptional, (7)
"Was a great house!! Clean, comfortable, and inviting. Close to Falmouth to get the ferry, close to Hyannis for dinner. Several great restaurants nearby! "
Totally Renovated Central AC Dog Friendly Near Golf

Spacious home in central location with beautiful patio, pool table, W/D, & AC

10.0 out of 10, Exceptional, (1)
"We loved our stay. This is the first time I have rented a house without a prior review. So glad we did! The house seemed brand new or very recently remodeled. The pool table and media area downstairs made the rainy day we had on the island a great one. We had a party of seven and plenty of space to spread out and relax. It was easy to walk to town but we also rented bikes to get around. I would highly recommend this home to anyone looking for a relaxing stay on Martha's Vineyard."
Spacious home in central location with beautiful patio, pool table, W/D, & AC

Ocean Edge Condo with Guest Passes to Pool, Golf, and Sports available!

9.2 out of 10, Wonderful, (5)
Ocean Edge Condo with Guest Passes to Pool, Golf, and Sports available!

Cape Cod Getaway – 3BR Sandwich Home, Walk to Beach, AC & WiFi

9.6 out of 10, Exceptional, (5)
"We had a phenomenal stay at this property. It was a group of friends coming together to watch a play at the Cape Playhouse. The house was pristine, beautifully decorated and everyone slept great on the beds and linens. Highly recommend!"
Cape Cod Getaway – 3BR Sandwich Home, Walk to Beach, AC & WiFi

Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!

8.2 out of 10, Very good, (23)
"The property was perfect for our family. It’s in a great location. We rented bikes and enjoyed being able to walk and bike to the beach and market. Thanks for letting us stay!"
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!

Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C

6.2 out of 10, (17)
"This property has not been well cared for or cleaned. Arrived to a very musty/moldy smell, trash outside, the walls were streaked with dead bug guts and then the stove didn't work!! It was a step above camping. You get what you pay for!"
Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C

Oceanfront Home with Deck + Cape Cod Bay views!

9.6 out of 10, Exceptional, (33)
"Enjoyed the location and the house very much"
Oceanfront Home with Deck + Cape Cod Bay views!

Charming Waterfront Cape Cottage with Private Beach and Beautiful Water Views

2.0 star property
Charming Waterfront Cape Cottage with Private Beach and Beautiful Water Views

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

8.6 out of 10, Excellent, (38)
"Close to the beach , clean and a wonderful Vineyard stay"
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Waterfront Home w/ Guest Cottage

10.0 out of 10, Exceptional, (1)
"I lined the view from the home and the safety in the area! Overall, great place for a big family !"
Waterfront Home w/ Guest Cottage

NEW LISTING! Spacious Brewster Beach Retreat – Walk to Multiple Beaches!

10.0 out of 10, Exceptional, (4)
"Awesome location and property! Mary was incredibly communicative and made our stay seamless. Highly recommend your next stay on the Cape to be here!"
NEW LISTING! Spacious Brewster Beach Retreat – Walk to Multiple Beaches!

Conveniently located and renovated cottage with lovely views & chef's kitchen

9.6 out of 10, Exceptional, (17)
"Clean and quiet "
Conveniently located and renovated cottage with lovely views & chef's kitchen

Pond Front Home with Private Dock!

9.8 out of 10, Exceptional, (49)
"Great home. Excellent layout especially for teens to have a little privacy in lower level room. "
Pond Front Home with Private Dock!

Walk to Beach | Parking for 2 Cars | Close to Town

10.0 out of 10, Exceptional, (7)
"We had a good time here. The cottage was small, but comfortable. Would stay here again."
Walk to Beach | Parking for 2 Cars | Close to Town

Victorian cottage overlooking downtown Oak Bluffs and the Harbor.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Nice nostalgic home Needs minor work (Toilet seats)(Middle room mirror )AC "
Victorian cottage overlooking downtown Oak Bluffs and the Harbor.
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