Holiday Homes in Southeast Massachusetts

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Southeast Massachusetts

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

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

10.0 out of 10, Exceptional, (164)
"Place was adorable perfect for what we needed. Perfect location, centralized for all your needs and wants"
The price is AU$536
includes taxes & fees
27 Aug - 28 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
Dining

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."
The price is AU$770
includes taxes & fees
1 Sept - 2 Sept
Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants
Hyannis Hideaway in Cape Cod
Paper towels

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 AU$1,033
includes taxes & fees
7 Sept - 8 Sept
Hyannis Hideaway in Cape Cod
Beautifully Renovated Main Street Cottage- Great Location
Dining

Beautifully Renovated Main Street Cottage- Great Location

10.0 out of 10, Exceptional, (117)
"We were thrilled to arrive at our property with everything as pictured but actually more charming in person. It is easily walkable to town and restaurants. Communication with the owner was easy and I can recommend it to anyone who wants to stay on Nantucket. "
Beautifully Renovated Main Street Cottage- Great Location
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!
2 bedrooms, free WiFi, bed sheets

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

8.4 out of 10, Very good, (24)
"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!
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Sun-loungers

3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.

10.0 out of 10, Exceptional, (2)
"Location is very convenient to lake scargo and corporation beach! House was extremely clean. Well appointed. Had games and beach toys and chairs. Great house for family. "
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Cozy 4 bedroom cottage in town, with parking
Terrace/patio

Cozy 4 bedroom cottage in town, with parking

2.0 star property
9.8 out of 10, Exceptional, (12)
"Great stay, would stay again "
Cozy 4 bedroom cottage in town, with parking
Ocean view spacious 5-bedroom Cape Cod style house with roof deck, AC, WiFi.
Sun-loungers, beach towels

Ocean view spacious 5-bedroom Cape Cod style house with roof deck, AC, WiFi.

9.8 out of 10, Exceptional, (116)
"The house is perfect for a large group! Excellent location & super unique, would definitely recommend!"
Ocean view spacious 5-bedroom Cape Cod style house with roof deck, AC, WiFi.
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Outdoor dining

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

10.0 out of 10, Exceptional, (161)
"Beautiful cottage , great location. Would love to stay again "
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
1 bedroom, iron/ironing board, Internet, bed sheets

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

8.0 out of 10, Very good, (39)
"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
Dining

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
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Fridge, microwave, oven, stovetop

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10.0 out of 10, Exceptional, (198)
"As always, lovely home. Perfect place."
The price is AU$916
includes taxes & fees
11 Sept - 12 Sept
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
Interior

Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

9.6 out of 10, Exceptional, (112)
"This property was as advertised. Right on a private beach, the views here are incredible. Make sure you plan to see a sunrise or sunset! Owner is very easy to work with and responsive. "
The price is AU$2,391
includes taxes & fees
21 Sept - 22 Sept
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
Love Sand, Madaket on the Beach , Lovely Seaside Home
Exterior

Love Sand, Madaket on the Beach , Lovely Seaside Home

10.0 out of 10, Exceptional, (52)
"We thoroughly enjoyed our two nights and are sad to leave. The property is iconically Nantucket. Its location - and the views- is spectacular. It is well equipped for a relaxing family or couples vacation. Hope we can make it back. "
The price is AU$2,496
includes taxes & fees
22 Sept - 23 Sept
Love Sand, Madaket on the Beach , Lovely Seaside Home
Walking to the beach. Bars and Restaurants.
Paper towels

Walking to the beach. Bars and Restaurants.

9.6 out of 10, Exceptional, (4)
"The home was very nice and in a convenient location. Ana was very helpful and quick with communications during our stay. Would highly recommend for anyone traveling to Oak Bluffs! "
Walking to the beach. Bars and Restaurants.
Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12
Fridge, microwave, oven, stovetop

Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12

10.0 out of 10, Exceptional, (2)
"The house was spotless and very well organized. My family and I loved our stay — it’s in a perfect location, close to everything: grocery stores, the beach, restaurants, and more. The owner is very communicative and responds right away to any questions. We would definitely love to come back!"
Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12
Town Neck Beach , Sandwich, MA, Cape Cod. Treehouse Brewery, marina, cc canal.
Exterior detail

Town Neck Beach , Sandwich, MA, Cape Cod. Treehouse Brewery, marina, cc canal.

9.8 out of 10, Exceptional, (78)
"This property was even better than expected! Our family of 5 adults all slept comfortably and the kitchen is very well stocked with anything you might need. "
Town Neck Beach , Sandwich, MA, Cape Cod. Treehouse Brewery, marina, cc canal.
Walk to Beach | Parking for 2 Cars | Close to Town
Beach

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

10.0 out of 10, Exceptional, (9)
"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
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Fridge, microwave, oven, stovetop

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2.0 star property
10.0 out of 10, Exceptional, (16)
"We’d loved our stay. Great house in a great neighborhood. Would love to stay here again!"
The price is AU$1,296
includes taxes & fees
16 Sept - 17 Sept
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Relax in this Sandwich Farmhouse - Cape Cod
Outdoor dining

Relax in this Sandwich Farmhouse - Cape Cod

10.0 out of 10, Exceptional, (1)
"The home itself was an excellent condition beautifully decorated the facilities were great. The backyard is beautiful. We did family games outback and there was a nice picnic table for us to sit on and it was just very peaceful. It was very close to the beach. It was also close to the Herritage Museum And Gardens, which is a wonderful thing. It was very close to a Stop & Shop two minute walk to the ice cream shop and the owners of the house were very accommodating and gracious and we just had a...
Relax in this Sandwich Farmhouse - Cape Cod
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

Holiday Inn Hyannis by IHG

Holiday Inn Hyannis by IHG

10/10 Excellent
"The location was perfect."
Bobbiejeanne 3-night trip
Posted 1 day ago
Holiday Inn Hyannis by IHG