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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 599 Cottages in Osterville with updated reviews, rates, and availability.

Charming Antique Boathouse Located Directly On Long Pond.
Exterior detail

Charming Antique Boathouse Located Directly On Long Pond.

9.8 out of 10, Exceptional, (93)
"The boat house was wonderful. It was perfect for me, right on Long Pond, everything I needed, within distance of all the places I went, the fall foliage was lovely and Lynn was fabulous. "
Charming Antique Boathouse Located Directly On Long Pond.
beachfront cottage at Chases Ocean Grove
On the beach, sun loungers

beachfront cottage at Chases Ocean Grove

9.8 out of 10, Exceptional, (24)
"Very rustic cottage, close to beach, relaxing"
beachfront cottage at Chases Ocean Grove
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, (111)
"To stay a block from the beach and look out the window at the water is the ultimate vacation! Even in winter this place is warm and inviting! The hosts are caring and communicative - just the best! This cottage lets you do just that"
Steps to the beach with an ocean view,
Craigsville beach cottage located .4 walking distance to the Beach!
Outdoor dining

Craigsville beach cottage located .4 walking distance to the Beach!

9.8 out of 10, Exceptional, (6)
"This was a great spot to stay for a small bachelorette party! We loved going to the beach, the outdoor shower and the kitchen and common area for hanging out. Host was super accommodating and responsive"
Craigsville beach cottage located .4 walking distance to the Beach!
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, (42)
"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
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
On the beach, sun loungers

Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views

10.0 out of 10, Exceptional, (156)
"Our second year visiting and just wonderful! Hope we can always make this our fall getaway!!"
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
Gorgeous Cottage steps from the beach
Beach nearby, sun loungers

Gorgeous Cottage steps from the beach

9.0 out of 10, Wonderful, (12)
"Great place to stay we loved it"
Gorgeous Cottage steps from the beach
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Beach nearby, sun loungers, beach towels

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

9.6 out of 10, Exceptional, (64)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.
On the beach, sun loungers, beach towels

5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.

10.0 out of 10, Exceptional, (20)
"Maushop is the perfect place for a family getaway right on the ocean. The property was clean and spacious for a tiny cottage. We had a wonderful time."
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.
Cape Code Waterfront Cottage
Fridge, microwave, oven, stovetop

Cape Code Waterfront Cottage

9.6 out of 10, Exceptional, (41)
"We had a wonderful time at the cottage. The cottage was beautiful, super clean, very tastefully decorated and a beautiful location. The host was always available and very helpful. I would definitely recommend this place and would happily return."
Cape Code Waterfront Cottage
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

6.2 out of 10, (17)
"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
Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower
Beach nearby, sun loungers, beach towels

Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower

10.0 out of 10, Exceptional, (23)
"This is our 2nd time at this property and we loved it again. The location is great. The property was super clean and inviting. Everything we needed to enjoy our stay. Just excellent across the board."
Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower
Oceanfront Cape Cod Gem w/ Balcony, Pets Welcome
TV, fireplace, books, smart speakers

Oceanfront Cape Cod Gem w/ Balcony, Pets Welcome

9.2 out of 10, Wonderful, (58)
"We had a wounderful long weekend. "
Oceanfront Cape Cod Gem w/ Balcony, Pets Welcome
ENCHANTING SEASIDE COTTAGE, STEPS TO THE BEACH!
On the beach, sun loungers

ENCHANTING SEASIDE COTTAGE, STEPS TO THE BEACH!

10.0 out of 10, Exceptional, (2)
"This TOTALLY renovated beach cottage was great. Very close to the beach and easy access to many restaurants."
The price is SAR 1,310
SAR 2,499 total
includes taxes & fees
18 Apr - 19 Apr
ENCHANTING SEASIDE COTTAGE, STEPS TO THE BEACH!
Lovely studio steps to the beach in Dennis port
On the beach, sun loungers

Lovely studio steps to the beach in Dennis port

The price is SAR 1,047
SAR 1,851 total
includes taxes & fees
16 May - 17 May
Lovely studio steps to the beach in Dennis port
Mermaid Cottage! beautiful propety!
Beach nearby, sun loungers, beach towels

Mermaid Cottage! beautiful propety!

10.0 out of 10, Exceptional, (100)
"Great property and location!"
Mermaid Cottage! beautiful propety!
2-bdrm Cottage | Close to Everything | Pet Friendly
Exterior

2-bdrm Cottage | Close to Everything | Pet Friendly

9.8 out of 10, Exceptional, (9)
"Many things to do nearby, beautiful town. The cottage was cozy, the beds comfortable. The views were great."
2-bdrm Cottage | Close to Everything | Pet Friendly
★The Islander | Steps From Water, Fire Pit, AC★
Terrace/patio

★The Islander | Steps From Water, Fire Pit, AC★

10.0 out of 10, Exceptional, (45)
"We stayed for a sisters weekend and it was just perfect!"
★The Islander | Steps From Water, Fire Pit, AC★
Charming 1 Bedroom Cottage Close To Beautiful Craigville Beach
Outdoor dining

Charming 1 Bedroom Cottage Close To Beautiful Craigville Beach

9.8 out of 10, Exceptional, (102)
"Comfortable cottage. Great location. "
Charming 1 Bedroom Cottage Close To Beautiful Craigville Beach
Adorable cottage on Cape Cod's historic Rt 6A
Property grounds

Adorable cottage on Cape Cod's historic Rt 6A

10.0 out of 10, Exceptional, (135)
"Very nice cottage and the location was great not a long drive to anything we went to."
Adorable cottage on Cape Cod's historic Rt 6A
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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Other property types in Osterville

Edgewater Beach Resort, a VRI resort
BBQ/picnic area

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (266)
"Check-in was great!"
The price is SAR 762
SAR 872 total
includes taxes & fees
24 Apr - 25 Apr
Edgewater Beach Resort, a VRI resort
InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (165)
"Beautiful property. Lots of amenities. Excellent appliances. Great location. View of the ocean & pool. Peaceful."
The price is SAR 552
SAR 631 total
includes taxes & fees
21 Apr - 22 Apr
InnSeason Resorts Captain's Quarters
The Club at New Seabury
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (315)
"Perfect little cottage!"
The price is SAR 709
SAR 812 total
includes taxes & fees
24 Apr - 25 Apr
The Club at New Seabury
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.