Osterville Vacation Rentals

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Our top choices for Osterville vacation rentals

Walk to Beaches & Dining: Classic Cape Cod Cottage

Walk to Beaches & Dining: Classic Cape Cod Cottage
3.0 star property
Dennis Port
The price is CA $152
CA $603 total
includes taxes & fees
Apr 20 - Apr 21
Walk to Beaches & Dining: Classic Cape Cod Cottage

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Sandwich
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our stay at this property. The view was amazing and had our own private beach to lounge at!"
United States
Sean H.
The price is CA $221
CA $557 total
includes taxes & fees
Apr 16 - Apr 17
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

Ocean View Room @ Beach Resort / Habitat *HOT TUB*

Ocean View Room @ Beach Resort / Habitat *HOT TUB*
Cape Cod
The price is CA $138
CA $420 total
includes taxes & fees
Apr 27 - Apr 28
Ocean View Room @ Beach Resort / Habitat *HOT TUB*

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, (6 reviews)
"Great place! Great host!"
United States
Moira C.
The price is CA $185
CA $408 total
includes taxes & fees
Apr 19 - Apr 20
Make this charming, modern retreat your home away from home!!

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (52 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is CA $123
CA $248 total
includes taxes & fees
Apr 16 - Apr 17
The Nantucket Room Unit - #2

The Crab Cottage@The Compound Beach Resort Habitat

The Crab Cottage@The Compound Beach Resort Habitat
Cape Cod
7.4 out of 10, Good, (6 reviews)
"Cozy clean property that allows pets. Outdoor fire pit area was great and perfectly private. I also loved that the property had a private beach area with lounge chairs. I used the grill and had brunch on the patio table. So nice to enjoy the water from so many parts of the property. Area is quiet and a 7 min walk to Onset Center where you can grab icecream or on some weekdays there’s an even in town. Close to plazas for other needs."
United States
l E.
The price is CA $34
CA $666 total
includes taxes & fees
Apr 16 - Apr 17
The Crab Cottage@The Compound Beach Resort Habitat

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Dennis
8.8 out of 10, Excellent, (3 reviews)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is CA $246
CA $538 total
includes taxes & fees
Apr 26 - Apr 27
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

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 CA $182
CA $814 total
includes taxes & fees
Apr 16 - Apr 17
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Falmouth
8.2 out of 10, Very good, (24 reviews)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is CA $178
CA $347 total
includes taxes & fees
Apr 16 - Apr 17
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre

Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre
Harwich
10.0 out of 10, Exceptional, (110 reviews)
"The hosts were so accommodating and lovely. The property is adorable and well appointed! Would stay again 100 percent. "
United States
rachel n.
The price is CA $207
CA $540 total
includes taxes & fees
Apr 23 - Apr 24
Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
The price is CA $197
CA $500 total
includes taxes & fees
May 8 - May 9
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

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

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
New Seabury
8.6 out of 10, Excellent, (91 reviews)
"This was the perfect home for our weekend getaway! Joyce was wonderful to work with. Perfect location and beautiful home, just what we needed!"
United States
Courtney R.
The price is CA $413
CA $851 total
includes taxes & fees
Apr 16 - Apr 17
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Quaint & Clean Cape Cod Loft

Quaint & Clean Cape Cod Loft
Bourne
10.0 out of 10, Exceptional, (18 reviews)
"Great location! Cute, quiet, neighborhood and so close to the beach. Perfect for our girls mini get away. "
United States
Jessica T.
The price is CA $220
CA $429 total
includes taxes & fees
Apr 16 - Apr 17
Quaint & Clean Cape Cod Loft

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, (130 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 CA $344
CA $526 total
includes taxes & fees
Apr 17 - Apr 18
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Cape Cod Oceanside Condo across from beach! Combine World Cup + Beach Holiday!

Cape Cod Oceanside Condo across from beach! Combine World Cup + Beach Holiday!
Dennis
8.6 out of 10, Excellent, (13 reviews)
"Room was as advertised, very close to the beach."
United States
Glen C.
The price is CA $138
CA $189 total
includes taxes & fees
May 3 - May 4
Cape Cod Oceanside Condo across from beach! Combine World Cup + Beach Holiday!

Pond View~ Abuts conservation and walking trails. There is fishing at the pond

Pond View~ Abuts conservation and walking trails. There is fishing at the pond
Dennis
10.0 out of 10, Exceptional, (129 reviews)
"Lovely comfortable place, as described, quiet location and perfectly located for accessing different parts of the Cape."
United States
david s.
The price is CA $276
CA $360 total
includes taxes & fees
May 13 - May 14
Pond View~ Abuts conservation and walking trails. There is fishing at the pond

Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck
Barnstable
8.0 out of 10, Very good, (3 reviews)
"We had a great stay in Hyannis! The location is great for catching a ferry to Nantucket or the vineyard, and Main Street is within walking distance. The backyard is also very peaceful for a cup of coffee in the morning! "
United States
Meghan H.
The price is CA $193
CA $544 total
includes taxes & fees
Apr 16 - Apr 17
Charming 3 bed room with magnificent views & large deck

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 CA $413
CA $1,045 total
includes taxes & fees
Apr 24 - Apr 25
Classic Cape House Walking Distance to the Beach - Many recent upgrades

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Brewster
10.0 out of 10, Exceptional, (44 reviews)
"Great place!"
United States
Michael P.
The price is CA $309
CA $536 total
includes taxes & fees
Apr 16 - Apr 17
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

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 CA $205
CA $718 total
includes taxes & fees
Apr 27 - Apr 28
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
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

Find out more about Osterville

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osterville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Osterville?

Yes, we give you a choice of vacation rentals in Osterville close to Stand Up & Paddle Cape Cod, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Osterville has to offer?

Coastal chic meets French Provençal in this newly renovated oceanfront home. : This vacation home rental outside of Osterville is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Osterville?

With 68 Expedia vacation rentals, you're sure to find just the right place for your Osterville stay.

What’s there to see and do in Osterville?

Cape Cod Beaches and Dowses Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Stand Up & Paddle Cape Cod. Public Beach and Main Street are a couple of places you'll find in the larger area.

What’s a vacation rental in Osterville like?

Vacation rentals are private properties you can book for a short or long stay in Osterville. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family trip.