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Our top choices for Osterville vacation homes

Make this charming, modern retreat your home away from home!!

Make this charming, modern retreat your home away from home!!
Wareham
9.8 out of 10, Exceptional, (8 reviews)
"Great place! Great host!"
United States
Moira C.
The price is AED 526
AED 1,141 total
includes taxes & fees
27 May - 28 May
Make this charming, modern retreat your home away from home!!

The Bunk Room @ The Compound ~Fish-Hunt-Breakfast

The Bunk Room @ The Compound ~Fish-Hunt-Breakfast
Cape Cod
The price is AED 184
AED 593 total
includes taxes & fees
1 Jun - 2 Jun
The Bunk Room @ The Compound ~Fish-Hunt-Breakfast

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (51 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is AED 485
AED 2,242 total
includes taxes & fees
25 May - 26 May
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Mermaid House @ The Compound Beach Resort Habitat

Mermaid House @ The Compound Beach Resort Habitat
Cape Cod
8.4 out of 10, Very Good, (8 reviews)
"Love the place but felt like would of been better if the owner wasn’t around not that they where bad or annoying just didn’t feel like we was like away felt like we was being watched but besides that loved it Wish barbecue was working and speaker in house was weird set up but besides that it was amazing"
United States
Oscar B.
The price is AED 184
AED 1,895 total
includes taxes & fees
1 Jun - 2 Jun
Mermaid House @ The Compound Beach Resort Habitat

Cape Cod's "Beach Rose"

Cape Cod's "Beach Rose"
Dennis
10.0 out of 10, Exceptional, (11 reviews)
"Great location. Good central location to explore the area."
United States
Robyn L.
The price is AED 645
AED 834 total
includes taxes & fees
26 May - 27 May
Cape Cod's "Beach Rose"

Cozy Riverfront Stay in Wareham

Cozy Riverfront Stay in Wareham
Wareham
10.0 out of 10, Exceptional, (3 reviews)
"Perfect for wedding guests. Spacious, clean and great viewWould definitely stay again"
United States
Karleen L.
The price is AED 725
AED 1,712 total
includes taxes & fees
25 May - 26 May
Cozy Riverfront Stay in Wareham

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
The price is AED 992
AED 3,610 total
includes taxes & fees
29 May - 30 May
4-bedroom house in lovely Edgartown..Centrally located

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Plymouth
10.0 out of 10, Exceptional, (134 reviews)
"Beautiful room and view, hosts were communicative and check in/out were easy. Would definitely stay here again!"
United States
Alexander L.
The price is AED 918
AED 1,407 total
includes taxes & fees
25 May - 26 May
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.0 out of 10, Wonderful, (24 reviews)
"Loved this property. "
United States
Carol S.
The price is AED 386
AED 1,788 total
includes taxes & fees
26 May - 27 May
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
Dennis
10.0 out of 10, Exceptional, (11 reviews)
"Wonderful place! Thank you so much! "
United States
Jess W.
The price is AED 760
AED 2,136 total
includes taxes & fees
31 May - 1 Jun
NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

Classic Cape House Walking Distance to the Beach - Many recent upgrades

Classic Cape House Walking Distance to the Beach - Many recent upgrades
Chatham
9.8 out of 10, Exceptional, (20 reviews)
"Mary was a wonderful host. The house was clean, close to beach and communication was wonderful! A great, relaxing stay!!"
United States
Kathleen T.
The price is AED 1,102
AED 2,766 total
includes taxes & fees
23 May - 24 May
Classic Cape House Walking Distance to the Beach - Many recent upgrades

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Barnstable
8.6 out of 10, Excellent, (8 reviews)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
The price is AED 551
AED 1,903 total
includes taxes & fees
25 May - 26 May
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Oldest Town of Cape Cod In The Historic District

Oldest Town of Cape Cod In The Historic District
Sandwich
9.0 out of 10, Wonderful, (19 reviews)
"We enjoyed our two night stay."
United States
Lonnie W.
The price is AED 430
AED 1,383 total
includes taxes & fees
25 May - 26 May
Oldest Town of Cape Cod In The Historic District

Home with spectacular panoramic ocean views from a bluff high above Cape Cod Bay

Home with spectacular panoramic ocean views from a bluff high above Cape Cod Bay
Plymouth
10.0 out of 10, Exceptional, (70 reviews)
"It was an amazing place to stay. The outside heater element looking over the Ocean was amazing! "
United States
Chance4 C.
The price is AED 1,752
AED 3,360 total
includes taxes & fees
26 May - 27 May
Home with spectacular panoramic ocean views from a bluff high above Cape Cod Bay

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Dennis
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Harwich
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location "
United States
Norman Y.
The price is AED 661
AED 2,283 total
includes taxes & fees
26 May - 27 May
Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

WATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed

WATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed
Bass River
10.0 out of 10, Exceptional, (107 reviews)
"Nice quiet neighborhood but close to a lot of different attractions. The home was perfect for our needs."
United States
Ryan T.
The price is AED 808
AED 2,568 total
includes taxes & fees
25 May - 26 May
WATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed

Private beach, hot tub, and dog friendly – The Keeper!

Private beach, hot tub, and dog friendly – The Keeper!
Brewster
9.8 out of 10, Exceptional, (17 reviews)
"The property is beautiful and in great location. The house is cozy and comfortable. We would stay there again!!!"
United States
Lori L.
The price is AED 3,620
AED 7,254 total
includes taxes & fees
12 Jun - 13 Jun
Private beach, hot tub, and dog friendly – The Keeper!

Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse
Harwich
9.8 out of 10, Exceptional, (11 reviews)
"Great location great property"
United States
Glenn M.
The price is AED 625
AED 1,531 total
includes taxes & fees
25 May - 26 May
Seaside Getaway - Harwichport Beachhouse

Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (12 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is AED 1,062
AED 2,531 total
includes taxes & fees
28 May - 29 May
Cozy Large Home in Harwich with Patio near Wequassett Resort
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 Osterville Hotel Reviews

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