Holiday Rentals in Osterville

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Holiday Rentals in Osterville

Quiet South Chatham 2-Bedroom House, Close To Beaches

9.4 out of 10, Exceptional, (3)
"We had a great stay. The location was perfect for visiting family, beach, and downtown Chatham. The house was spotless. We wouldn't hesitate to stay again!"
The price is €614
includes taxes & fees
18 Jul - 19 Jul
Quiet South Chatham 2-Bedroom House, Close To Beaches

Newly Renovated Guest House For 10 Near The Beach!

10.0 out of 10, Exceptional, (4)
"Space was great for our family/friends gathering Location perfect for events we were attending on the Cape"
The price is €1,188
includes taxes & fees
13 Jul - 14 Jul
Newly Renovated Guest House For 10 Near The Beach!

Luxe Lakefront Retreat ★ Sauna ★ Media Rm ★ Kayaks ★ Bikes ★ Steps to Bike-Path★

Luxe Lakefront Retreat ★ Sauna ★ Media Rm ★ Kayaks ★ Bikes ★ Steps to Bike-Path★

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

9.6 out of 10, Exceptional, (43)
"Everything was great clean beautiful house as advertised "
The price is €684
includes taxes & fees
22 Jul - 23 Jul
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

Starfish Cottage★0.4mi walk Beach & Village★Pet Friendly★Bikes★Fireplace★Firepit

9.8 out of 10, Exceptional, (53)
"Great location. Easy access to shopping and restaurants. Owner very accomodating and friendly!!"
The price is €913
includes taxes & fees
5 Aug - 6 Aug
Starfish Cottage★0.4mi walk Beach & Village★Pet Friendly★Bikes★Fireplace★Firepit

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

10.0 out of 10, Exceptional, (155)
"Place was adorable perfect for what we needed. Perfect location, centralized for all your needs and wants"
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Walk to Sea Street Beach! Firepit| Dogs OK| A/C!

9.6 out of 10, Exceptional, (4)
"Our vacation at Kim and Dave’s cottage was fabulous, location to the beach and restaurants were exactly what we needed, fenced in back yard with a deck a fire-pit and grill is perfect if you’re bringing young ones or a fur-baby… thank you again to Dave and Kim,"
Walk to Sea Street Beach! Firepit| Dogs OK| A/C!

Dennis Family Retreat: Private Pool, Sauna & Beach Fun!

The price is €5,846
includes taxes & fees
13 Jul - 14 Jul
Dennis Family Retreat: Private Pool, Sauna & Beach Fun!

NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

9.8 out of 10, Exceptional, (9)
"Our family had a wonderful time and truly enjoyed the home. The family voted and this is our favorite home out of the past 4 yrs of renting in the Cape! Beautiful, clean, and great location tucked in a quiet neighborhood but close to it all."
NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

Cozy Coastal Retreat West Dennis

2.0 star property
Cozy Coastal Retreat West Dennis

3 Mi to Beach: Historic Farmhouse on Cape Cod!

3 Mi to Beach: Historic Farmhouse on Cape Cod!

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

West Dennis Central - 5 bed, 3 bath, 2 kitchen huge yard! Two hot tubs!

9.4 out of 10, Exceptional, (20)
"The house is very cute and had everything we needed. The location is great and the owner was super responsive."
West Dennis Central - 5 bed, 3 bath, 2 kitchen huge yard! Two hot tubs!

Townhouse Two Bed Suite

Townhouse Two Bed Suite

Beachfront - Sauna - Screened Patio - 2 King Beds - Dogs Encouraged!

10.0 out of 10, Exceptional, (2)
"This is definitely one of our better stays and it really felt like a home away from home. Cozy, with a beautiful lakefront view and incredible amenities, I highly recommend staying here."
The price is €1,216
includes taxes & fees
25 Jul - 26 Jul
Beachfront - Sauna - Screened Patio - 2 King Beds - Dogs Encouraged!

Near Mayflower! Pool & Hottub! Dogs OK! Slps 10!

2.0 star property
10.0 out of 10, Exceptional, (3)
"The house was very clean and spacious. Our group of ten had plenty of room to spread out. The home had great amenities to keep everyone happy. Our hosts were also responsive. We recommend! "
The price is €2,020
includes taxes & fees
2 Aug - 3 Aug
Near Mayflower! Pool & Hottub! Dogs OK! Slps 10!

"Awesome Vacation while staying at "HomeAway" from Home"

8.4 out of 10, Very good, (74)
"Great spot for a beach getaway!"
The price is €223
includes taxes & fees
20 Jul - 21 Jul
"Awesome Vacation while staying at "HomeAway" from Home"

Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

8.0 out of 10, Very good, (3)
"Our family stayed here for a quick Cape get away at the end of summer. The host was responsive and kind. The property was in a great location with a kitchen that had everything we needed. Great spot"
The price is €592
includes taxes & fees
7 Aug - 8 Aug
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

Newly renovated home near beaches with fire pit, AC, electric vehicle charging

10.0 out of 10, Exceptional, (2)
"Nina’s place was the perfect spot for our quick family beach getaway! From the moment we arrived, our little one felt right at home. The space is beautifully designed with a calm, beachy feel and so thoughtfully laid out—especially for families with young kids.Everything we needed for a smooth and relaxing stay was already there: a cozy floor bed, a nightlight, and a sound machine made bedtime easy, and kid-friendly plates, trays, and utensils were all set up at just the right height. The...
The price is €828
includes taxes & fees
7 Aug - 8 Aug
Newly renovated home near beaches with fire pit, AC, electric vehicle charging
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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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?

Oldest Town of Cape Cod In The Historic District: This holiday home rental outside of Osterville is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Osterville?

With 76 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.