Discover a selection of 500 vacation rentals in Winter Harbor that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and kitchens. Prices start at $125 per night, and houses and cottages are popular options for a stay in Winter Harbor. Either way, you'll find a rental for everyone's needs.

How many vacation rentals are available around Winter Harbor?

Our 2020 property listings offer a large selection of 647 vacation rentals around Winter Harbor. From 367 house rentals to 185 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a seaside property in Winter Harbor?

Don't just spend a morning at the beach. Round up your clan and find a place on its doorstep! The sound of the surf and remarkable blue vistas? We'd say it's a no-brainer! Vrbo has 253 beachside rental properties to take your pick of. Searching for a different setting? See if any of our other properties steal your heart. Our range here includes:

  • 174 village vacation rentals.
  • 155 ocean-view vacation rentals.
  • 153 oceanfront vacation rentals.

Can I rent a house in Winter Harbor?

Forget about standardized, cookie cutter chain-hotel rooms. Our house vacation rentals offer a personal touch — and all the space you could need! There are 366 options available on Vrbo. Prices start at $67 per night. Or perhaps you'd rather choose one of the area's other lodging options, such as:

  • Cottage: 139 vacation homes. Prices start from $50 per night.
  • Cabin: 33 vacation homes. Prices start from $79 per night.
  • Apartment: 32 vacation homes. Prices start from $109 per night.

Can I stay in Winter Harbor in a large group?

Sometimes it can be tricky finding time to spend with your nearest and dearest. A getaway is an ideal opportunity to get together. If you were planning to stay together, Vrbo has options for you. 100 house vacation homes are listed. Presently, they're the leading choice here for sizeable groups. Properties around this area that can cater for large groups include:

  • Searching for vacation homes that can hold 6 people? We have 334 that will suit. Prices start from $113 per night.
  • Need a vacation rental for 8 people? We have 222 that will be perfect. The starting price is $115 a night.
  • Organizing a trip away with a group of 10? We've got 98 vacation homes that will be ideal. Prices begin at just $184 per night.

You and all your besties will be well looked after when you book your Winter Harbor travels through us!

Where are the cheapest rentals in Winter Harbor?

Cut down on those pesky accommodation expenses by organizing your stay with Vrbo. You'll find plenty of great rentals and save loads of cash! Otter Creek is an awesome area to check out if you want to keep a handle on your budget. Vrbo has 30 rentals, and the average price is a modest $211 per night. You'll find another 31 Vrbo rentals waiting to be booked in or around Somesville. The average price in this area is $213 a night.

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