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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 593 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)
"Enjoyed coffee on the enclosed porch overlooking ocean. Great communication with owner. Bathroom nicely done. Very clean, cute, well setup for a cottage. "
beachfront cottage at Chases Ocean Grove
Steps to the beach with an ocean view,
Beach nearby, 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)
"Courtney's house is in a fantastic location. Easy access to downtown Hyannis for shopping and nightlife, walkable to beaches with fantastic swimming. The house is newly renovated, but maintains the charm of a home with some history in the area. Sweet backyard with a patio set up to enjoy outdoor dining and lounging. The neighborhood feels secluded, but is really near all the summer happenings. Well stocked kitchen, smart use of a small space. I can't say enough about our fantastic stay. I have...
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)
"What an amazing little place this was! We thoroughly enjoyed our stay at this hidden gem. Right on the water, we enjoyed early morning coffee watching the fish jump and the birds float along the water. We slept up in the loft and the view out the window at sunrise was just breathtaking. We will definitely be booking here again! Thank you for sharing your little slice of heaven with us!"
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)
"Perfect getaway"
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)
"Great property in great location on Cape Cod. 30 min drive for ferry to Nantucket. 2 minute walk to Beach within neighborhood. Cozy and quiet. Would not hesitate to stay again. "
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)
"My wife and my Yorkie, and I loved our stay. This is a beautiful home with the best views of Swan Pond. The entire back of the home has floor to ceiling windows so you can see the pond from the living area and the bedroom. We are looking forward to next year’s stay! Thank you, "
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)
"We did not stay. Place was a dump No one has called us We are not paying It is illegal not to have carbon / smoke detectors We went to condos at new seabury"
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 second time at this property. It is as described. Beautifully updated. Location could not be better!! One street away from where my grandparents used to live. Such great memories!"
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!
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 1,309
SAR 2,499 total
includes taxes & fees
31 Mar - 1 Apr
ENCHANTING SEASIDE COTTAGE, STEPS TO THE BEACH!
Lovely studio steps to the beach in Dennis port
Sun loungers

Lovely studio steps to the beach in Dennis port

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)
"The Mermaid Cottage has everything you’d want. It’s close to shopping and beach areas. The house is stocked with so many extras, like strollers, high chair, fire pit and outdoor patio. "
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)
"Beautiful cottage, very clean and comfortable. Very peaceful and quiet! Weather wasn't the best for sitting outside to enjoy nature, but it was beautiful nonetheless. Bonnie is an excellent host! We definitely will return!"
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, (44)
"I was travelling with my 3 sisters from Canada heading towards Martha's Vineyard for a sister's reunion. We all appreciated the cleanliness and the attention to detail. The space was well appointed. The fridge ice maker did not work well so having some ice cube trays would have been helpful. I highly recommend The Islander."
★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)
"The cottage is truly adorable. Comfy, cozy and fully equipped for my stay which was over 30 days. The owners who is the property manager is attentive and wonderful to work with. Everything was first rate such flat screen TV, high speed WIFI, plush white bathroom towels, the spices, the furniture and the comfort of the bed. I love to walk. Easy to cross 6A and walk the Long Pasteur trails every day. Beach is 1 mile walk down Bone Hill Road. Cottage is in a perfect location; 2 miles to Barnstable...
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, (261)
"beach was close by on property..the indoor/outdoor pool was nice..the 2 bedroom was overly spacious and well kept ,overall very nice place too stay"
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, (162)
"Girl at front desk was awesome!!!"
The price is SAR 441
SAR 504 total
includes taxes & fees
31 Mar - 1 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, (314)
"Excellent after hours check-in process. Clean and comfy townhouse. Wonderful amenities. "
The price is SAR 630
SAR 721 total
includes taxes & fees
31 Mar - 1 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.

Frequently asked questions

How much do cottages in Osterville cost?
Cottages in Osterville range between SAR 1,309 and SAR 1,309 per night. These properties offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Osterville?
Osterville offers multiple cottages with a total average guest review rating of 9.4. Sun Retreats Peters Pond is a top option if you’re a fan of nature and an unhurried pace. Guests staying at this 2.5-star stay can access a swimming pool and a barbecue grill. 11 Mashpee - 2 Bedroom Cottage is another recommended choice. This 3-star cottage comes with a barbecue grill and a golf course.
How many cottages are there in Osterville?
There are 593 cottages in Osterville. No matter if you’re traveling with the little ones or organizing a weekend retreat with your pals, Expedia will help you find the right place to immerse yourself in nature.
Why book your cottage in Osterville with Expedia?
Booking a cottage in Osterville is as easy as deciding on your travel dates and picking your ideal place for outdoor relaxation and recreation. From ritzy retreats to low-cost properties and cottages that have perks like free WiFi, Expedia has something for all traveler styles. As for the best deals around? We’ve got you covered!
How can I find cheap cottages in Osterville?
A great way to get cheap cottages in Osterville is with Expedia’s useful filter tool. Narrow down your search by budget, star rating and amenities to secure unbeatable prices in just a few keystrokes.