
Holiday rentals in Osterville
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Top-rated holiday rentals in Osterville
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Serene Haven w/ No Shared Spaces | Cape Cod
My peaceful 2-bedrooms, 1 bathroom residential private apartment (Entire Main Level) has everything you need for your Marstons Mills trip. The home comes with Wi-Fi, self-check-in, and free parking. During your stay, you will enjoy the privacy of zero shared spaces. Free cleaning once per week for stay 6 days or greater. Our Airbnb is within walking distance to eateries, gift shops, and other community staples. An ideal base to explore Marstons Mills, Cape, and Islands. Bring the whole family.

Quintessential Waterfront Historic Cottage
Set in a historic district and on a quiet pond shore, create memories with family and friends that will last a lifetime. Enjoy quintessential New England views from every angle. Coffee, restaurants, shopping & a fresh spring water fountain within a short walk to village center and under a mile to the nearest beach. Spend time walking the local area, exploring Cape Cod and relaxing in an atmospheric setting. Each room has been curated in a timeless tone, with relaxation and comfort in mind.

Cozy Cottage - Steps to Craigville Beach
Come enjoy the beauty of Centerville, MA and Craigville Beach in our summer home! This clean and cozy cottage is just a 5 minute stroll from the beach and provides guests with the perfect setting for a relaxing vacation. Perfect for couples, families, and small groups of friends, this cottage can comfortably sleep 2-5 guests and offers all the necessary amenities for your ideal vacation. Enjoy a cold drink on the back deck or soak up the rays on the beach- you have found your destination!

Cozy Coastal Cottage With Sprawling Sea Views
Take in endless views of the ocean walking up to this quaint cottage. Here, the pace is leisurely – sip coffee on the deck, watch the sunrise, and swim in the warm waters of Nantucket Sound just outside. We make changes yearly! A new marble bath was just installed! Close by is downtown Hyannis to shop and eat, mini golf, a water park, ferries to the islands, harbor tours, biking, and more. You will be at peace and filled with serenity staying here on Cape Cod. Can't wait to host you!

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

Cozy 1-level fenced yard Craigville Beach 2000sqft
Welcome to Midori On The Cape! This freshly renovated 3-bedroom, 2-bath, Cape-style house features 2000 sq ft all in one level in a quiet neighborhood, 15000 sqft lot with fenced in flat backyard, fire pit, string lights, BBQ-grille. Quick access to Craigville Beach, Cape Cod Mall, vibrant Hyannis downtown and ferry terminal to Martha's Vineyard and Nantucket Island 2 living rooms, 2 dining areas, 3 super-sized bedrooms. Perfect for family staycation and gathering, get away.

600 ft Walk to Ocean! 2nd floor Renovated Cottage!
Quaint second floor 785 sq ft unit w/ private entrance. 3 tenants MAX with ONE parking spot. 600 ft to shared neighborhood private beach. Great spot for couples or small families. NO guests without prior permission in house or on private beach. Queen bed in master, one twin bed in 2nd bedroom. Eat-in kitchen/living room. Bathroom w/ stand-up shower. Stocked w/ linens, towels, kitchen supplies. Island ferry boats - 1m. Historic Main St.- 1.2

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!

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 hammock. Just a short walk to the ocean, beaches, the library and the general store.

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 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!

Osterville Charming Cottage in the Heart of Wianno
This Nantucket style cottage is tucked away down a private lane but right in the heart of Wianno, the most prestigious section of Osterville. Just a stroll to the Village and less than a mile from Dowses Beach make this seaside bungalow a perfect retreat. Occupancy tax of 14.45% applicable. Certificate Number: C0089770200
Popular amenities for Osterville holiday rentals
Stay near Osterville's top sights
Other great holiday rentals in Osterville

Walk to Lake Wequaquet Beach | 4BR Cape Cod

Charming Cozy Coastal Retreat|Pet Friendly|EV

Three Ships Cove | Walk to Craigville Beach

Charming Ranch, Near Beaches & Town in Osterville

Spacious Cape getaway near iconic Craigville Beach

Bright beachy 2 kings. Linens/beach pass

Chez-Po_Barnstable A/C House

Idyllic Getaway for 2-Historic 6A-4 min. to beach
When is the best time to visit Osterville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 253 | € 253 | € 253 | € 264 | € 286 | € 361 | € 421 | € 435 | € 305 | € 294 | € 295 | € 316 |
| Avg. temp | 0°C | 0°C | 3°C | 7°C | 12°C | 17°C | 21°C | 21°C | 18°C | 13°C | 8°C | 3°C |
Quick stats about holiday rentals in Osterville

Total holiday rentals
Explore 150 holiday rentals in Osterville

Nightly prices starting at
Osterville holiday rentals start at € 67 per night before taxes and fees

Verified guest reviews
Over 3,710 verified reviews to help you choose

Family-friendly holiday rentals
130 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
140 of Osterville holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Osterville rentals

4.9 Average rating
Osterville stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Family-friendly rentals Osterville
- Rentals with a washing machine and dryer Osterville
- Rentals with a fireplace Osterville
- Rentals with a patio Osterville
- Rentals with a firepit Osterville
- House rentals Osterville
- Pet-friendly rentals Osterville
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- Rentals with pools Osterville
- Rentals with beach access Osterville
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Easton Beach
- Onset Beach
- Second Beach
- Coast Guard Beach
- The Breakers
- Pinehills Golf Club
- Sandy Neck Beach
- South Shore Beach
- New Silver Beach
- Lighthouse Beach
- Cahoon Hollow Beach
- Nickerson State Park
- Cape Cod Inflatable Park
- Sea Gull Beach
- Popponesset Peninsula
- Scusset Beach State Reservation
- Skaket Beach
- Race Point Beach




