Osterville, Barnstable vacation rentals

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Top-rated vacation rentals in Osterville, Barnstable

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Guest favorite

Guesthouse in Barnstable

5.0 out of 5 average rating, 111 reviews

Modern Fireplaced Carriage House with Beach Permit

Feel at home & relax in our new one bedroom carriage house. Modern yet classic Cape Cod style and elegance. Rest easy on a new Stearns & Foster king size mattress with designer linens and furnishings. Cozy up to the fireplace and flat screen TV. Custom bathroom, Bosch laundry units and small deck. Kitchenette with dishwasher drawer, under cabinet refrigeration, microwave, toaster, Keurig coffee maker, Starbucks coffee and various teas. We offer beach chairs, bags & towels for your convenience.

Aug 24 – 31

R9,478 ZAR per night

Guest favorite

Guest suite in Oak Bluffs

4.94 out of 5 average rating, 308 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

Feb 4 – 11

R1,970 ZAR per night

Guest favorite

Condo in Dennis

4.99 out of 5 average rating, 172 reviews

Studio, 300 yards to Glendon Beach; Seahorse#2

Newly renovated, 250 sq ft studio at Near Beach Rentals. 300 yards to Glendon Beach means you can head to the beach in the morning and you're close enough to walk back for lunch. Fully furnished studio includes a queen bed and a fold down couch, kitchen with stove, fridge, coffee maker and microwave, air conditioning, 40" smart TV, newly renovated bathroom, Wifi, and access to the shared courtyard with grills and furniture. **(6) total units makes NBR a great place for larger gatherings!!!

Oct 12 – 19

R2,400 ZAR per night

Guest favorite

Apartment in Falmouth

4.98 out of 5 average rating, 115 reviews

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

Oct 25 – Nov 1

R1,340 ZAR per night

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 150 reviews

Cozy and Secluded Apartment/Seasonal garden view

Walk across your private patio through sliding glass doors to your private garden retreat in this spacious studio. A large bathroom is just off the kitchen. This brand new apartment is designed for your perfect vacation or retreat from city life. If you are working from home - try working from Cape Cod! A desk awaits you - leave your computer set up and ready! Not the best apartment for disabilities - the entrance is in the back and there is a step up into the shower.

Dec 14 – 21

R1,820 ZAR per night

Guest favorite

Cottage in Barnstable

4.99 out of 5 average rating, 122 reviews

Beach Glass Cottage - Pond Front

Come stay at the Beach Glass Cottage! A pristine pond front, completely renovated and tastefully decorated, 3 bedroom, 2 bathroom cottage in the heart of Hyannis. Truly the perfect get-a-way for family and friends. The Beach Glass Cottage is tucked away from the action, but within walking distance to Main Street Hyannis, which features eclectic shops, restaurants, bars, ice cream with mini golf and the Cape Cod Melody Tent is a short walk from the cottage as well.

Jan 2 – 9

R4,436 ZAR per night

Guest favorite

Cottage in Bourne

5.0 out of 5 average rating, 143 reviews

140 Steps to Beach with Water Views

This small rustic unique cottage is ready for you to enjoy on Buttermilk Bay. It is located within a cape style cottage community that offers a private association beach. There are water views from both the living room and deck. Grab the provided beach chairs, water tubes, cooler and walk a 140 steps from the deck to the beach. You can also Walk or Bike on Cape Cod Canal, 5 min. Close to restaurants, hiking trails and Cape Cod Bridge -5 min away. 20% off wk.

Apr 13 – 20

R2,591 ZAR per night

Guest favorite

Guest suite in Barnstable

4.97 out of 5 average rating, 153 reviews

Dog friendly, 2.4 ml bch, 1 bedrm, stdio priv entr

Kids under 12 stay for free! Msg me details but dont incl children in count. Sunny, clean 2 rm studio sleeps 4 + w/door separating sleep areas Priv fenced in yard 5 to 10 min bches ponds 10-15 min to Lrg bches Separate entrance 3 beds: 1 queen 2 tw kitchenette w/micro, sm frig toaster, toaster oven, hot plate personal grill, small deck, fenced in yard w/swing set. Your dogs will be completely separate from my 3 little dogs. Yards are private.

Mar 14 – 21

R2,993 ZAR per night

Guest favorite

Apartment in Barnstable

4.99 out of 5 average rating, 231 reviews

Your dog will love it here and you will too.

If you love to travel with your dog (dogs), like I do, then this is the perfect place for you and your dog. We have a large fenced in yard for your dog to play in and for you to relax in with your dog. We have a one bedroom apartment with a full kitchen, bath, living room and dining area When you book would you PLEASE let me know whether or not you will be traveling with a dog and if you are what breed of dog will you be bringing. Thanks!

Feb 19 – 26

R2,505 ZAR per night

Guest favorite

Guesthouse in Barnstable

4.87 out of 5 average rating, 106 reviews

Relaxing Cottage in Centerville Village

Welcome to my home! The cottage is located in Historic Centerville Village, it's a welcoming, bright and relaxing, studio space; perfect for a couple, or individual, to getaway on Cape Cod. Salt Tide Cottage is a private guesthouse with off-street parking and a serene outdoor space. It sits behind the main house with its own back yard space with fire pit. Just a short walk to the ocean, beaches, the library and the general store.

Sep 6 – 13

R3,092 ZAR per night

Guest favorite

Home in Barnstable

5.0 out of 5 average rating, 107 reviews

Cape Cod Cotuit Cottage, 3 Bed Near Beaches

5 star rental Cottage in the beautiful village of Cotuit! This quaint 3-bedroom cottage is perfect for a getaway for friends and family. It is just a short distance to nearby beaches, local fresh market, walking trails, Cape Cod league baseball stadium, shopping and restaurants. Relax on the private patio area and enjoy the peaceful, natural setting. Bring along your dog too!

Aug 31 – Sep 7

R8,319 ZAR per night

Guest favorite

Guest suite in Barnstable

4.9 out of 5 average rating, 145 reviews

3 room apartment on quiet street

This is an apartment in the basement of our home. It is a walkout with nearly 800 SF of space and full size windows looking out on a private backyard. Located close to Craigville Beach, historic downtown Hyannis, the Cape Cod Melody Tent and island ferries. Please read the "more info about this space" to get more details.

Dec 27 – Jan 3

R1,736 ZAR per night