Search Osterville Cottage Rentals from CA $276

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Osterville Cottages

Steps to the beach with an ocean view,
On the beach, sun loungers, beach towels

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (126)
"Nice home, great views and very relaxing stay."
Steps to the beach with an ocean view,
Steps to the Ocean! Perfect Location!!!
Beach nearby, sun loungers

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (219)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!
Peaceful Cozy Water Front Cottage. Step back in time and ENJOY
Smart TV

Peaceful Cozy Water Front Cottage. Step back in time and ENJOY

9.6 out of 10, Exceptional, (50)
"The cottage has a beautiful view everything we needed, and it was very relaxing"
Peaceful Cozy Water Front Cottage. Step back in time and ENJOY
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
Smart TV, DVD player

Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks

9.8 out of 10, Exceptional, (177)
"Very happy with our stay"
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
Pets allowed with warmer weather around the corner! Plan your Cape Cod vacation!
Exterior

Pets allowed with warmer weather around the corner! Plan your Cape Cod vacation!

9.8 out of 10, Exceptional, (32)
"Great location, excellent communication with owner!!"
Pets allowed with warmer weather around the corner! Plan your Cape Cod vacation!
Steps to private Beach, Golf Course, AC, tandem Kayak for Guests
Beach nearby, sun loungers

Steps to private Beach, Golf Course, AC, tandem Kayak for Guests

9.4 out of 10, Exceptional, (26)
"Enjoyed our stay: clean, modern and great location."
Steps to private Beach, Golf Course, AC, tandem Kayak for Guests
Tranquil waterfront cottage. Recently remodeled, with relaxation in mind.
Smart TV, table tennis, books

Tranquil waterfront cottage. Recently remodeled, with relaxation in mind.

10.0 out of 10, Exceptional, (48)
"Cool cottage. Great location. Awesome host. Stay here."
Tranquil waterfront cottage. Recently remodeled, with relaxation in mind.
Quintessential 2-bedroom Cape cottage with salt marsh views near Seagull Beach
Sun loungers

Quintessential 2-bedroom Cape cottage with salt marsh views near Seagull Beach

9.2 out of 10, Wonderful, (5)
Quintessential 2-bedroom Cape cottage with salt marsh views near Seagull Beach
Seaview cottage near Ocean Beaches & The Skipper!
Outdoor dining

Seaview cottage near Ocean Beaches & The Skipper!

Seaview cottage near Ocean Beaches & The Skipper!
Mermaid Cottage! beautiful propety!
Beach nearby, sun loungers, beach towels

Mermaid Cottage! beautiful propety!

10.0 out of 10, Exceptional, (102)
"Great property and location!"
Mermaid Cottage! beautiful propety!
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach
Property grounds

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

5.8 out of 10, (27)
"Great location and private beach access. Charming enclave perfect for our weekend getaway."
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach
Cozy family-friendly cottage on beautiful Shining Sea bike trail
Fridge, microwave, oven, stovetop

Cozy family-friendly cottage on beautiful Shining Sea bike trail

10.0 out of 10, Exceptional, (4)
"This cottage is charming and inviting. The hosts have outdone themselves with their attention to detail. This place has everything you could want or need. We hope to return someday! "
Cozy family-friendly cottage on beautiful Shining Sea bike trail
New Listing in Brewster - 3 beds, 2 baths, 0.2 mile walk to Private Beach
Exterior detail

New Listing in Brewster - 3 beds, 2 baths, 0.2 mile walk to Private Beach

10.0 out of 10, Exceptional, (4)
"If I could give it more stars I would. Owners were helpful and kind. House was immaculate and the location was 10/10. It had AC, an outdoor shower and a brand new screened in porch that we basically lived in. It was perfect. We can’t thank you enough. "
New Listing in Brewster - 3 beds, 2 baths, 0.2 mile walk to Private Beach
beachfront cottage at Chases Ocean Grove
On the beach, sun loungers

beachfront cottage at Chases Ocean Grove

9.8 out of 10, Exceptional, (29)
"Very rustic cottage, close to beach, relaxing"
beachfront cottage at Chases Ocean Grove
Gorgeous Cottage steps from the beach
Beach nearby, sun loungers

Gorgeous Cottage steps from the beach

8.0 out of 10, Very good, (18)
"Great place to stay we loved it"
Gorgeous Cottage steps from the beach
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
Beach nearby, sun loungers, beach towels

Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

8.8 out of 10, Excellent, (28)
"Jim is fantastic to work with."
The price is CA $291
CA $543 total
includes taxes & fees
Sep 21 - Sep 22
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.
On the beach, sun loungers, beach towels

Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.

10.0 out of 10, Exceptional, (28)
"We had a great trip and look forward to staying there again. Location is the best part!"
The price is CA $276
CA $876 total
includes taxes & fees
Sep 17 - Sep 18
Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Dining

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

9.6 out of 10, Exceptional, (69)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Cozy Beach Cottage
Beach nearby, sun loungers, beach towels

Cozy Beach Cottage

9.8 out of 10, Exceptional, (50)
"The property was prepared, very thoughtful and had everything you could think of for a wonderful beach Island stay. The only downside was cable because I’m addicted to TV and I would’ve appreciated at least a smart TV that I could connect my own Netflix. "
Cozy Beach Cottage
1 bedroom "Doll house"
Exterior

1 bedroom "Doll house"

10.0 out of 10, Exceptional, (4)
"Bill was an amazing host and the proactive communication was great. the house was nice and clean and a perfect stay! "
1 bedroom "Doll house"
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

Sea Crest Beach Resort

Sea Crest Beach Resort

10/10 Excellent
"Beautiful place to stay "
Stephanie 2-night trip
Posted 7 hours ago
Sea Crest Beach Resort