Vacation rentals in Orleans

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Top-rated vacation rentals in Orleans

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Top guest favourite

Cottage in East Orleans

4.99 out of 5 average rating, 90 reviews

Hobbit Cottage with Marsh View

Are you special enough to stay at the Hobbit Cottage? All of our tenants have been magical so far and we want to continue that trend! This cute little house is on a lovely marsh where you will hear birdsong while you enjoy the ever changing view of the gentle wetland. A mini paradise nestled in a quiet neighborhood, it is an easy bike ride or a short drive to Nauset Beach. Tiny and cozy, the cottage has every amenity for a comfortable stay! (7 Day SATURDAY - SATURDAY Minimum in July and August.)

Guest favourite

Home in Orleans

4.96 out of 5 average rating, 23 reviews

Antique Cottage with Path to Arey’s Pond

Relax at this unique and tranquil escape. Our small but charming one bedroom cottage offers a compact kitchen and a small full bath. A true antique from 1850, the unit is updated but remains quintessential Old Cape Cod. Private yard, outdoor shower, fire pit, laundry, and access to Arey’s Pond 350 yds down private path. A pet friendly getaway for a couple looking to relax in an ideal Orleans location. Close to Nauset Beach, Orleans, Chatham, shops & great dining. A super place to vacation.

Guest favourite

Apartment in East Orleans

4.9 out of 5 average rating, 20 reviews

Cape Escape Studio - Unit A

Studio Apartment with private entrance, king sized bed, full bath with shower. There is also a kitchenette with fridge, microwave, Keurig coffee maker and dinnerware. TV and Wifi are also included in the unit. Two Miles from Nauset or Skaket Beach The property is walking distance to downtown Orleans for shopping and restaurants. The Rail Trail Bike path is less than one mile away. This unit is attached to a private house with multiple units, please reach out to host with additional questions.

Top guest favourite

Home in East Orleans

5 out of 5 average rating, 21 reviews

Peaceful Nauset Beach Sanctuary

Imagine driving down a quiet private dirt road behind one of the nicest beaches on Cape Cod. Enter the property through a gate and walkway and you’re in your own private sanctuary. The cottage feels like a treehouse looking onto the tidal marsh behind Nauset Beach. Inside you will feel the vibes of a nostalgic cape cod cottage with modern amenities and style. Chill out on the deck. Take a 10 minute walk to a private section of Nauset Beach or drive to our free association Nauset parking lot.

Superhost

Home in Orleans

5 out of 5 average rating, 3 reviews

Steps to Rock Harbor, Fully Renovated Cottage

Welcome to Rock Harbor! Nestled just steps from the picturesque Rock Harbor in Orleans, our newly renovated Cape Cod cottage offers the perfect blend of coastal charm and modern comfort. Ideally located between the vibrant villages of the Mid Cape and the natural beauty of the Outer Cape, it’s a great home base for day trips to Provincetown, the Cape Cod National Seashore, and local favorites like Chatham and Hyannis. Perfect for families, friends, or couples seeking a relaxing getaway.

Top guest favourite

Guest suite in East Harwich

4.99 out of 5 average rating, 614 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

Guest favourite

Guest suite in East Orleans

4.91 out of 5 average rating, 195 reviews

Charming Old Cape Cod

Indulge in relaxation and leisure at Snowtop on the Town Cove. The charming retreat features a private entrance, a spacious bedroom with a king size bed, a full bath, and a sunlit living room with a dining table offering picturesque views of the Town Cove. Guests are encouraged to bring their kayaks and paddleboards, as a town landing is conveniently located nearby. Nestled on a tranquil road, Snowtop is just 3 miles from stunning Nauset Beach and 2 miles from the center of Orleans.

Superhost

Home in Orleans

4.89 out of 5 average rating, 9 reviews

Private Beach - 3 bedroom

Welcome to The Lookout at Pleasant Bay! This enchanting 2.5-acre property offers access to a private beach. Enjoy a beautiful flagstone patio with a pergola and a cozy fire pit for evenings under the stars. Inside, a unique 100-foot tower serves as a game room, perfect for gatherings. The property blends the charm of "Ye Olde Cape Cod" with modern comforts like air conditioning and smart TVs. Experience the perfect mix of natural beauty and contemporary living at The Lookout!

Top guest favourite

Home in East Orleans

5 out of 5 average rating, 73 reviews

4 Season Cottage, Nauset Beach, tennis court

A four-season, luxurious, cottage-style retreat near the glorious beaches on the North spit of Nauset Beach, off Nauset Heights. Tennis court, ample grounds, walking neighborhood, and easy beach access. This Property is shared with two seasonal cottages. Perfect for getaways, the cottage is designed for a couple or individual. While there are two twins downstairs, these are appropriate for children, a friend, or a relative who will not be jealous of the king room upstairs.

Guest favourite

Home in Eastham

4.97 out of 5 average rating, 186 reviews

The Sea Captain's Carriage House

The 1840s Carriage House has been beautifully remodeled. The first floor has a living room, dining area, kitchen, and powder room with washer/dryer. The backyard deck has seating for four and a Weber gas grill. Upstairs, the large, elegant bedroom features a king-sized bed, sitting area, reading nook/twin bed, writing desk, and ensuite bathroom with shower. The half acre property offers beautiful gardens for you to enjoy and a delicious outdoor shower.

Guest favourite

Home in East Orleans

4.94 out of 5 average rating, 16 reviews

Orleans, MA Luxury Getaway

Enjoy the best the Cape has to offer! Stay at this hidden gem in Orleans, MA. Easy access to Nauset Beach and Little Pleasant Bay. Large, luxurious, and family friendly with a big yard in a quiet neighborhood. Enjoy our gazebo, firepit, outdoor grill, outdoor patio dining, and outdoor shower. Inside, luxuriate in this 4 bed 4 bathroom with a modern kitchen, breakfast nook, dining room, and living room. Washer and dryer included in basement.

Top guest favourite

Apartment in Eastham

4.95 out of 5 average rating, 261 reviews

National Seashore Escape

There is no interaction required with hosts during stay. 1/4 mile to National Seashore Salt Pond Visitor Center and 2.0 miles to Coast Guard Beach, rated America's 6th best beach in 2019 by Dr Beach. The studio is above the garage with a private entrance private bath with shower. Queen bed, wifi, whisper quiet mini split a/c no window unit, tv. There is a kitchenette with refrigerator, microwave, coffee maker, toaster, sink, no stove.