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Compare 442 Cottages in Osterville with updated reviews, rates, and availability.

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

8.6 out of 10, Excellent, (79)
"Great location but the place was dirty. Need a better cleaning service. "
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (201)
"Loved the rental. Perfect setting, loved being able to walk 2 minutes and be on the beach! So much nicer than a hotel room, very clean and comfortable for the four of us. Steve was a very kind and helpful host!"
Steps to the Ocean! Perfect Location!!!

Cozy 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. "
Cozy beachfront cottage at Chases Ocean Grove

Grandma's Cottage: Olde Cape Cod at its best. Steps to the beach. Dog-friendly!

8.8 out of 10, Excellent, (18)
"Could use some updates and repairs but overall a nice cottage close to the ocean / beach, shopping and restaurants. Outdoor shower was great and nice hot water! Furniture in living space could be better. More comt seating and the table and chairs inside weren't needed and just took up space. Extra countertop would be good as it was hard to cook and the stove needs to be leveled. Some kind of high top bar with stools would have been great and a different arrangement with the living room...
Grandma's Cottage: Olde Cape Cod at its best. Steps to the beach. Dog-friendly!

Cape Cod Cottage steps from Private Beach

10.0 out of 10, Exceptional, (32)
"Property was great. Small but we were out a lot. Great location and ownner was very helpful and responsive"
Cape Cod Cottage steps from Private Beach

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

8.8 out of 10, Excellent, (26)
"The property was great and walkable to the beach, but needs a few upgrades. "
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

Walking distance to Private Beach! Charming Cottage North of Cape Cod.

10.0 out of 10, Exceptional, (5)
"It’s a bargain for your budget and it’s definitely worth it! Helena is the best host on this app! Will definitely rent from her in the future!"
Walking distance to Private Beach! Charming Cottage North of Cape Cod.

Hear the sound of the surf

2.0 star property
10.0 out of 10, Exceptional, (2)
"very cozy, very clean. easy to keep toasty warm. really is just steps to the beach. tiny but great kitchen. "
Hear the sound of the surf

Oceanside 2 - SD335

9.6 out of 10, Exceptional, (13)
"House is set behind a dune. dune is a little steep, especially climbing back up. Kind of tough for the elderly. Set up of the house was good for 2 seniors. Many restaurants close by. Quiet area."
Oceanside 2 - SD335

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

9.8 out of 10, Exceptional, (167)
"Absolutely loved this property. The house was small, clean, and right on the beach. Perfect for 2 people. The only reason I’m giving 4 stars is because I just went to book this place again for next year and the price has been raised to $600 a night. So sad, I wanted to go back but not at that price. "
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks

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

Lovely Cape Cottage 2 bedroom with private beach and central air.

10.0 out of 10, Exceptional, (44)
"Such a cute and comfortable place. We enjoyed the neighborhood and the beach down the street. Owner was really responsive if we needed anything "
Lovely Cape Cottage 2 bedroom with private beach and central air.

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

9.6 out of 10, Exceptional, (100)
"A very comfortable few days on the mid-Cape. Great location, great little cottage. Quiet, private, clean. I'd do it again!"
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Lovely oceanfront cottage with deck, grill, & panoramic views

9.0 out of 10, Wonderful, (85)
"Fantastic view, cant say enough about sunrise and sunset. Nice away from it all spot close enough to places to go fora really good balance. The road in isa back road on the cape going any faster than 5mph will rattle you around but totally worth the slow roll in. "
Lovely oceanfront cottage with deck, grill, & panoramic views

Walk to the Beach! Two bedroom cottage in Swifts Beach community.

9.8 out of 10, Exceptional, (18)
"We had a great vacation! The property was just as shown. Lots of space for a 2 bedroom and very convenient to restaurants and the beaches! "
Walk to the Beach! Two bedroom cottage in Swifts Beach community.

Dennis Port Beach House 40 Steps to the Sand. 3 Bedroom

9.8 out of 10, Exceptional, (18)
"This is a beautiful, clean, charming cottage right across from a nice beach. We were very happy overall with this choice. It worked very well for our family of 4. The negatives: When we arrived at midnight after flying to Boston from Colorado we were surprised to learn that there were no linens, no towels, no tissues or paper towels, and no toilet paper in the entire place (there was half a roll of toilet paper left from previous renters). The toilet requires a specialty TP because it’s old...
Dennis Port Beach House 40 Steps to the Sand. 3 Bedroom

Chappy cottage with private beach

10.0 out of 10, Exceptional, (14)
"This cottage was the perfect little getaway for our family to base our first visit on Chappy. We loved being able to walk to the beach and appreciated the cleanliness of the cottage as well as its charm. "
Chappy cottage with private beach

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

Dog-friendly beach cottage on Harwich's main street with large lawn

8.8 out of 10, Excellent, (28)
"Perfect home and location. Thank you!"
Dog-friendly beach cottage on Harwich's main street with large lawn

Cape Cod Dune Cottage Spectacular Ocean Views, over the dune to a private beach

10.0 out of 10, Exceptional, (87)
"Spectacular view of the ocean from the spacious deck, especially at sunset. (My partner teared up from the sheer beauty when she first saw it!) Also enjoyed the zero-gravity chair on the deck, and the binoculars. The interior is thoughtfully decorated, and we appreciated the investment in the additional half-bath (especially when we entertained a family of four for dinner). Kitchen is well-supplied (yay, multiple cutting boards!), and we were grateful for the variety of pillows with each...
Cape Cod Dune Cottage Spectacular Ocean Views, over the dune to a private beach
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

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower

9.4 out of 10, Exceptional, (38)
"We enjoyed the time spending there. That is mostly fit us well due to the circumstance for which we were there. My wife liked every minute of it and so did I; but I simply wish there were some coffee there, along with the coffee maker. So, I wouldn’t have to go out just for that, the first night we got there. "
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (310)
"accommodation was good but cleanliness could have been better. Not bad but some areas needed more attention. Good restaurant and bar service on Thursday. No restaurant available on Saturday."
The price is SAR 601
SAR 688 total
includes taxes & fees
28 Jan - 29 Jan
The Club at New Seabury

The Cove At Yarmouth

3.0 star property
9.2 out of 10, Wonderful, (220)
"This is my wife and my favorite spot to just come and relax in the off season and get some great hot chocolates from our favorite bakery in town. "
The price is SAR 484
SAR 554 total
includes taxes & fees
26 Jan - 27 Jan
The Cove At Yarmouth
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?
Rates for cottages in Osterville range between and per night. No matter your budget, you’re sure to find the perfect place to relax and reconnect with nature. 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 has multiple cottages with a total average guest review rating of 9.4. Sun Retreats Peters Pond is a fantastic option if you love nature and an easy-breezy pace. Guests staying at this 2.5-star stay will enjoy amenities such as a barbecue grill and a swimming pool. 11 Mashpee - 2 Bedroom Cottage is another popular pick. This 3.5-star cottage has a barbecue grill and a playground.
How many cottages are there in Osterville?
Choose from 442 cottages in Osterville. Whether you’re taking a trip with the little ones or planning a weekend escape with your besties, Expedia can help you find the perfect space to enjoy the surrounding nature.
Why book your cottage in Osterville with Expedia?
Booking a cottage in Osterville is as easy as entering your travel dates and selecting your ideal place for a vacation in nature. From high-end retreats to low-cost properties and cottages that come with perks like free WiFi, Expedia has something for all traveler styles. As for the best offers around? We’ve got you covered!
How can I find cheap cottages in Osterville?
Expedia is here to help you look for cheap cottages in Osterville. To book your ideal stay in a few quick clicks, use our convenient filter tool to refine your search by star rating, budget and amenities.