Vacation rentals in Orleans

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Top-rated vacation rentals in Orleans

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Top guest favorite
The image displays four sections of the cottage. A cozy sleeping area features a full-size bed with soft linens. A bright kitchen with marble counters is visible, alongside a comfortable living space with seating. An outdoor deck with furniture showcases a partially fenced yard.
Tiny home in Dennis Port
4.83 out of 5 average rating, 511 reviews

★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes

Welcome to SAND PEBBLE COTTAGE! We are PET FRIENDLY! ($25/nt) This 300sq.ft "TINY HOUSE" is 0.4 mi from the ocean beach & 1/2 mi from Dennisport village At the end of a cul-de-sac, this tiny cottage has everything you need ✅ 4/10mi to beach & village ✅ Kitchen w/marble counters ✅ 2 Bike ✅ Deck w/furniture & charcoal BBQ ✅ Parking-2 cars ✅ Separate bedroom ✅ Full A/C ✅ Bring your sheets/towels-we do not provide linens ✅ Pet friendly-only 1 pet as the cottage is tiny $25/nt

Top guest favorite
A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.
Home in Harwich Port
4.98 out of 5 average rating, 113 reviews

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Sun filled open concept living room with a large kitchen island. Great for families ! Less than 4 min drive to Red River beach and Bank street Beach. 3 min drive to Wychmere Beach Club wedding venue. Close to Harwich Port downtown. Centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy a hike to Harwich Thompson's field Conservation area. Close to bike trail

Top guest favorite
A charming cottage with a shingle exterior is framed by a vibrant yard. A white picket fence encloses flower beds, and a small patio features an umbrella for shade. A welcoming pathway leads to the front door, surrounded by greenery and a manicured lawn.
Cottage in Chatham
4.97 out of 5 average rating, 280 reviews

Cozy Cottage

Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property

Top guest favorite
A charming single-story home is presented with light grey shingles and dark blue shutters. A paved pathway leads to the front door, framed by manicured green lawns and landscaped flower beds. Trees and shrubs add to the serene outdoor environment.
Cottage in Harwich Port
4.95 out of 5 average rating, 400 reviews

Newly renovated Cape Coddage! Location! Location!

Newly renovated! Harwichport home- 2 min walk to beach, sleeps 10. Located right by Bank St Beach In Harwichport! Walk 1-2 minutes to the beach or walk 1-2 minutes in the other direction to Main Street where you will find shops and restaurants. Ember, The Port, 3 Monkeys, Beer Garden, and Mad Minnow. This home is in the dream location. Pull in and you don't need to drive until you leave. Walkable to Wychmere beach club. This home is often shared by guests of events celebrated at Wychmere.

Top guest favorite
A spacious backyard features a well-maintained lawn, surrounded by lush greenery. A wooden deck with seating overlooks the area, complemented by colorful flower pots. A hammock is nestled between trees, inviting relaxation. Comfortable chairs are arranged for outdoor enjoyment.
Guest suite in Harwich
4.99 out of 5 average rating, 635 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.

Top guest favorite
Guesthouse in Brewster
4.95 out of 5 average rating, 131 reviews

Brand new, on a secret pond

Welcome to our chic guest house. This brand-new retreat includes a bedroom with king bed, a living room with a sofa bed, smart TV, sleek breakfast bar, and a contemporary bathroom with rainshower and a heated towel rail. Steps away the beach invites you to relax by the water of a semi-private pond next to the rail trail. Welcome to a retreat that strikes the perfect balance between contemporary luxury and the tranquility of nature – for those who appreciate the finer things in life.

Top guest favorite
A bright living area features large windows overlooking a scenic marshland and ocean view. A cozy cream-colored couch and an armchair are positioned near a glass coffee table, inviting relaxation. Natural light fills the space, enhancing the tranquil ambiance.
Home in Chatham
4.97 out of 5 average rating, 159 reviews

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

Top guest favorite
A cozy living area features a light-colored sofa adorned with blue cushions and a small wooden coffee table in front. A lamp stands next to the sofa. Natural light filters in through a large window, illuminating the warm wood flooring.
Guest suite in Orleans
4.94 out of 5 average rating, 102 reviews

Spacious Guest Suite Close to Town

Our second floor guest suite is on a quiet street, within walking distance to the center of town and a quick drive to ocean and bay beaches. Featuring an open floor plan and high ceilings, the suite includes a living/dining room, kitchenette, reading nook, private bath, and spacious bedroom. Guests have their own outside entrance and tiny deck. Our family of four (+dog & cat) live downstairs. We are happy to provide tips and recommendations, or let you enjoy your privacy.

Superhost
A charming exterior of the Carriage House features weathered shingle siding and a cupola on the roof. Surrounded by landscaped gardens, the entrance showcases a well-kept pathway and a mix of greenery and blooming flowers, creating a welcoming ambiance.
Home in Eastham
4.96 out of 5 average rating, 194 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 favorite
A bright living area features a high cathedral ceiling with wooden beams. Two comfortable sofas are arranged around a coffee table, and a wood-burning stove is positioned beside large glass doors that open to the outdoor deck. Natural light streams in from the windows.
Home in Wellfleet
4.87 out of 5 average rating, 121 reviews

A Cape Escape with Water Views from Every Room

Come enjoy our family vacation home! A beautiful, serene escape perched above the salt marsh - with lovely views from every room, and a huge 1,000 square foot outdoor deck. Sleeps 8 comfortably. A 10-minute drive to charming Wellfleet center, and just an 8-minute drive to ocean beaches. NOTE: BEDSHEETS, LINENS & BATH TOWELS ARE INCLUDED IN PRICE! This is our family ''getaway'' - a place of treasured memories. We hope it can be the same for you!

Superhost
The cottage's exterior is framed by lush greenery, featuring a spacious deck with a large blue umbrella and picnic table. Vibrant flower pots add color, while stepping stones lead towards the entrance, inviting guests to enjoy the peaceful surroundings.
Cottage in North Eastham
4.9 out of 5 average rating, 239 reviews

Classic Cape Cod Cottage

No cleaning fee! 15 min walk to the best bayside beach, Thumpertown Beach. The cottage is in a very peaceful wooded setting. A beautiful, charming 2 bedroom cottage 15 min walk to Thumpertown Beach. It's situated on a triple sized lot, close to the outer Cape's favorite attractions. Eastham is known as the Gateway to the Cape Cod National Seashore. Please note, from June 13 to September 6 we have a 7 night minimum from Saturday to Saturday.

Top guest favorite
A prominent sign marks the entrance to Cape Cod National Seashore Salt Pond Visitor Center. Surrounded by greenery, the sign features bold lettering identifying the center and includes the National Park Service emblem, set against a backdrop of trees and a clear blue sky.
Apartment in Eastham
4.96 out of 5 average rating, 276 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.

Popular amenities for Orleans vacation rentals

When is the best time to visit Orleans?

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Avg. priceG$75,354 GYDG$80,168 GYDG$69,493 GYDG$69,493 GYDG$65,935 GYDG$79,959 GYDG$96,286 GYDG$96,913 GYDG$67,191 GYDG$66,772 GYDG$68,028 GYDG$72,423 GYD
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Frequently Asked Questions

  • What types of vacation rentals are available in Orleans?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Orleans. From over 320 house rentals to over 30 cottage rentals, we've got you covered.

  • Where should I stay in Orleans?

    Make yourself at home in Orleans by choosing from our most frequently booked neighborhoods. We have over 310 vacation rentals in South Orleans, and over 740 vacation rentals in East Orleans.

  • Are there vacation rentals with a dedicated workspace in Orleans?

    Yes! Work meets play with ease at over 240 vacation rentals in Orleans featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Orleans?

    Four-legged friends are welcome in Orleans. Choose from more than 140 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in cottage rentals in Orleans?

    Experience the best of Orleans with our cottage rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do cottage rentals in Orleans have a bbq area?

    Absolutely! We offer over 20 cottage rentals with a bbq area in Orleans. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Orleans have air conditioning?

    Absolutely! We offer over 30 cottage rentals with air conditioning in Orleans. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Orleans have wifi?

    Absolutely! We offer over 30 cottage rentals with wifi in Orleans. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly cottage rentals in Orleans?

    Orleans has more than 20 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Orleans have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Orleans. Enjoy a tailored experience with all the comforts you desire.

  • Are there Orleans house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 house rentals with pools in Orleans, available on Airbnb. Make a splash and soak up the sun in style!

  • What are the most popular amenities for Cottage Rentals in Orleans?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 30 homes with air conditioning, over 20 homes with a bbq area, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Orleans

  • Total vacation rentals

    Explore 380 vacation rentals in Orleans

  • Nightly prices starting at

    Orleans vacation rentals start at G$10,466 GYD per night before taxes and fees

  • Verified guest reviews

    Over 10,780 verified reviews to help you choose

  • Family-friendly vacation rentals

    300 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 130 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    220 properties have a dedicated workspace

  • Wi-Fi availability

    370 of Orleans vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Orleans rentals

  • 4.8 Average rating

    Orleans stays are highly rated by guests—averaging 4.8 out of 5!