Osterville Holiday Rentals

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Holiday Rentals in Osterville

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
9.2 out of 10, Wonderful, 27 reviews
"We really enjoyed our stay. There were a few issues. We couldn’t get in through the front door at all we had to go in through the garage. There were no potholders for cooking. Missing sugar for morning coffee. Napkins and tissues also unavailable. The only major concern that was an inconvenience neither of the bathrooms had heat. Thank you We will definitely be back again"
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Holly Tree Resort by VRI Americas
3.0 star property
9.2 out of 10, Wonderful, 301 reviews
"Loved this property "
Holly Tree Resort by VRI Americas
Cape Winds Resort by VRI Americas
3.5 star property
8.8 out of 10, Excellent, 393 reviews
"Awesome"
The price is NZ$285
includes taxes & fees
12 Jun - 13 Jun
Cape Winds Resort by VRI Americas
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Oceanside 2 - SD335
9.8 out of 10, Exceptional, 10 reviews
"This little cottage was perfect for my wife and I. We started coming to the Cape in the Fall because the Summers are too crowded for us there. This cottage was nearly perfect for our stay. It is nestled in a small loop off of the road where there are a few cottages. Not bad in October but probably more bustling in the Summer. The only thing I didn't like was that the path down to the beach is alongside of this cottage and when coming off the beach, everyone is passing the back deck. Otherwise,...
Oceanside 2 - SD335
The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, 283 reviews
"Beautiful location with all amenities !"
The price is NZ$366
includes taxes & fees
6 Jun - 7 Jun
The Club at New Seabury
Historic Cape home with private pool, tennis court, summer kitchen, & game barn
9.8 out of 10, Exceptional, 16 reviews
"Lots of fun for more than one family to stay!"
Historic Cape home with private pool, tennis court, summer kitchen, & game barn
The Cove at Yarmouth by VRI Americas
3.5 star property
9.2 out of 10, Wonderful, 278 reviews
"I like how it has indoor pool and access inside so you dont have to go outside in winter to find pool"
The price is NZ$375
includes taxes & fees
12 Jun - 13 Jun
The Cove at Yarmouth by VRI Americas
Dog-friendly home with firepit, deck & washer/dryer - walk to Sandy Neck Beach
9.4 out of 10, Exceptional, 31 reviews
"Beautiful home. Beautiful beaches nearby. Lovely fenced yard."
Dog-friendly home with firepit, deck & washer/dryer - walk to Sandy Neck Beach
Oceanfront Cape Cod Vacation Rental: Beach Access!
9.2 out of 10, Wonderful, 45 reviews
"Property was lovely as advertised. Oceanfront, clean, spacious. Nothing beats hearing the crashing waves at night on the upstairs bedroom patio. Highly recommended!"
Oceanfront Cape Cod Vacation Rental: Beach Access!
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista
9.6 out of 10, Exceptional, 110 reviews
"It was a perfect place, the balcony by was in the right position to watch sunrise and sunsets. Condo was very clean and comfortable."
The price is NZ$1,096
includes taxes & fees
12 Jun - 13 Jun
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista
Quaint condo near private beach access with fireplace - close to dining
9.0 out of 10, Wonderful, 39 reviews
"It was the perfect location for our anniversary getaway! My wife and I would certainly stay here again!! Five stars!!!"
The price is NZ$641
includes taxes & fees
27 Jun - 28 Jun
Quaint condo near private beach access with fireplace - close to dining
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
9.0 out of 10, Wonderful, 33 reviews
"All the things we needed: beach, comfortable place to sleep, eat and shower. Appreciated the extra beach chairs! Plenty of towels for showering. Plenty of movies and games if there’s a bad weather day - we were lucky to have none of those! We hope to return. Thanks for sharing your place!"
The price is NZ$702
includes taxes & fees
6 Jun - 7 Jun
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
Steps to the Ocean! Perfect Location!!!
10.0 out of 10, Exceptional, 172 reviews
"We enjoyed our stay at Steve's property. The location is wonderful and there are so many things to do on The Cape! There were fairly minor issues that did not detract from the overall stay. And when Steve was contacted he made great efforts to fix the issue(s)."
Steps to the Ocean! Perfect Location!!!
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
9.8 out of 10, Exceptional, 152 reviews
"Perfect for two. Loved having the ocean at our doorstep. The Murphy bed was sturdy and comfortable. The small kitchen area was likely not suitable for gourmet cooking, but could serve well for basic vacation meals (We ate all our meals out. ). Overall, the cabin was clean and neat and cozy. The early May weather was cool but pleasant. Some of our time was spent (with jackets on) sitting on the deck drinking morning coffee while watching the ocean and the few people who walked by. We also did...
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
Cozy beachfront cottage at Chases Ocean Grove
10.0 out of 10, Exceptional, 11 reviews
"My friend and I had a wonderful time at your cottage. My friend had not visited the Cape in a long time so it was fun for both of us to go exploring. And it was great that the cottages were right on the beach so we did not have to drive anywhere to soak up the sunshine."
Cozy beachfront cottage at Chases Ocean Grove
Cape Cod Vacation Home Rental - Walk to Beach
10.0 out of 10, Exceptional, 7 reviews
"We loved being able to walk to cafes, restaurants and the bookstore and the proximity of the bike path meant that we didn't need our car much at all. We rode bikes to lunch spots, the beach, and to the pickleball courts. The house was tidy and had everything we needed."
Cape Cod Vacation Home Rental - Walk to Beach
New House,2 Masters,Steps to Beach, Main Street, Ferry, Central AC, WiFi, Linens
9.8 out of 10, Exceptional, 125 reviews
"The accommodations were clean, spacious, with a deck large enough for all if us and a great, green yard. The listing description was accurate and then some with the beach being and easy 5 min walk. We highly recommend! Lynn and Jim F, 06/2024."
New House,2 Masters,Steps to Beach, Main Street, Ferry, Central AC, WiFi, Linens
InnSeason Resorts Captain's Quarters
3.5 star property
9.6 out of 10, Exceptional, 145 reviews
"Large, comfortable suite, plenty of amenities"
The price is NZ$369
includes taxes & fees
10 Jun - 11 Jun
InnSeason Resorts Captain's Quarters
Oceanfront home with private beach, large deck, & washer/dryer - dog-friendly
9.6 out of 10, Exceptional, 5 reviews
"Thank you for a great stay! Beautiful house and location. We had a great time!"
The price is NZ$4,152
includes taxes & fees
6 Jun - 7 Jun
Oceanfront home with private beach, large deck, & washer/dryer - dog-friendly
THE BOAT HOUSE LOFT ~ THE CAPE'S BEST VALUE IN A RELAXING WATERFRONT VACATION!
9.2 out of 10, Wonderful, 85 reviews
"This is a true get a way for 2. Larry was informative and hospitable. What a view!"
THE BOAT HOUSE LOFT ~ THE CAPE'S BEST VALUE IN A RELAXING WATERFRONT VACATION!
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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.

Other types of properties in Osterville you may be interested in

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Osterville holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Osterville. 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 Osterville. 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 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 holiday 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 Osterville short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Osterville?

Yes, there are holiday rentals in Osterville close to Stand Up & Paddle Cape Cod, or you can select a more secluded option if you're looking for a relaxing stay.

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

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower: This highly rated holiday home rental in Osterville offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals are there in Osterville?

With 99 Expedia holiday rentals, you're guaranteed 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 wider area.

What’s a holiday rental in Osterville like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osterville. Holiday rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a family trip or a small group gathering.

Recent reviews of Osterville properties
Expedia verified reviews