Orleans Vacation Rentals

(26 rentals)
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3 BR | 2 BA | Sleeps 7 | Quick View

Distance to beach: 0.1 miles to Bakers Pond

$255

avg/night

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Key Amenities

  • Kid friendly

About this property

''Hilltop'' is a bright and airy newly-renovated home with easy access to beautiful Bakers Pond. Tucked up on a hill in a quiet neighborhood, this home has living areas on 3 levels, a fully-equipped kitchen and dining area (with bay windows) and opens to a large wraparound deck. Fresh comfortable furnishings, ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly
  • Oceanfront

About this property

This beautiful, sunny farmhouse located near the heart of Orleans is an antique home that has modern updates inside and a gorgeous surrounding yard. Very private with ample parking. Walking path to Gould Pond for birdwatching and nature walks.The house is open, airy, very clean and well cared for. ...

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Orleans House

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3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.8 miles to Skaket Beach

$416

avg/night

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Key Amenities

  • Kid friendly

About this property

Light & bright 3-bedroom + den home with central A/C near Skaket Beach! Lovely 2900 sq. ft. Cape on a quiet lane 8/10 mile from the sandy shores of Cape Cod Bay. Main level features a spacious main bedroom with full bath and laundry area, a large living room, separate den (with queen pullout), an ...

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Orleans House

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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.0 miles to Mayflower Point

$216

avg/night

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Key Amenities

  • Kid friendly

About this property

WATERFRONT COTTAGE! Nestled on two acres in Mayflower Point is this absolutely lovely, newly renovated cottage. Light and bright with cottage character throughout, painted exposed beams, skylights and glorious views out to Pleasant Bay. Two bedrooms, one with a queen bed, the other with a bunk-bed set, ...

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Orleans House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Nauset

$338

avg/night

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Key Amenities

  • Kid friendly

About this property

Great privacy in East Orleans! Enjoy this lovely 3-bedroom, 2-bath contemporary home offering a bright and open floor plan and updated furnishings. Front-to-back living room with fireplace and a great screened porch open onto a spacious wraparound deck. This great vacation spot is gracefully tucked up ...

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Orleans House

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4 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.2 miles to Mill Pond

$559

avg/night

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Key Amenities

  • Kid friendly

About this property

Salt waterfront home located in the Ocean Harbor Association in East Orleans. This newly-furnished home is set on over an acre of beautiful multi-level grounds with frontage and views of Little Cove. Enjoy kayaking right from your backyard, access to the association tennis courts or deepwater boating ...

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Orleans House

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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Skaket

$175

avg/night

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Key Amenities

  • Kid friendly

About this property

Location, Location! Popular duplex cottages very close to Skaket Beach on Cape Cod Bay. Simple and beachy, each unit has a private deck and central air-conditioning! Both share the enclosed outdoor shower. No washer/dryer, but there's a clothesline for bathing suits and towels. Each unit has a bath with ...

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Orleans House

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4 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.6 miles to Skaket

$390

avg/night

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Key Amenities

  • Kid friendly

About this property

Walk to Skaket Beach! Spacious home tucked away at the end of a quiet cul-de-sac only 6/10ths of a mile from the sandy shore of Cape Cod Bay via a neighborhood path. Offering great privacy on 1.3 acres, the highlights of this home are its wonderful family room with cathedral ceiling and wood stove, new ...

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Orleans House

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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.0 miles to Mill Pond

$186

avg/night

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Key Amenities

  • Kid friendly

About this property

Spectacular Location! An outstanding waterfront spot offering exceptional privacy. Want to unplug? This simple, rustic cottage (no wifi, no TV) is on a peninsula surrounded by salt water and has views of Mill Pond. Launch your kayak or boat from its shore to access Nauset Inlet and to the beautiful sandy ...

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Orleans House

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3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 0.0 miles to Pilgrim Lake

$392

avg/night

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Key Amenities

  • Kid friendly

About this property

At the end of a private lane lies your secluded vacation retreat on tranquil Pilgrim Lake. Just 60 feet from the decks and living room window is your private lakefront with swim float for boating, fishing or swimming. The main deck, overlooking the water with comfortable outdoor furniture and gas grill, ...

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Property Type

Orleans House

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1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.3 miles to Nauset Harbor

$166

avg/night

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Key Amenities

  • Kid friendly

About this property

Adorable guest house located in a beautiful, quiet area about 3/10ths of a mile from Nauset Harbor. Consisting of 528 square feet, the cottage offers much! The cozy living/dining/kitchen area , includes a queen sofabed and A/C unit. The bedroom has a king (easily converted into 2 twins, if you prefer) ...

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Orleans House

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3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Skaket

$238

avg/night

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Key Amenities

  • Kid friendly

About this property

Location, Location! Popular duplex cottages very close to Skaket Beach on Cape Cod Bay. Simple and beachy, each unit has a private deck and central air-conditioning! Both share the enclosed outdoor shower. No washer/dryer, but there's a clothesline for bathing suits and towels. Each unit has a bath with ...

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Orleans House

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4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 0.8 miles to Crystal Lake

$421

avg/night

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Key Amenities

  • Kid friendly

About this property

Crystal Lake-- Designed to look like an illustration from a children's fairytale, this gracious and comfortable vacation home promises a magical vacation any time of the year. Enter through lush gardens into a surprisingly spacious, fully air conditioned home designed with relaxation, convenience, and ...

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Orleans House

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4 BR | 3 BA | Sleeps 11 | Quick View

Distance to beach: 3 miles to Nauset Beach

$565

avg/night

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Key Amenities

  • Kid friendly

About this property

Wonderful East Orleans property with newer furnishings and central A/C, perfect for family and friends of all ages. Enjoy this terrific 4 bedroom home that affords space for everyone. The main house has a spacious king bedroom on the 1st floor with a full bath and walk-in shower. The 2nd floor features ...

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Orleans House

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5 BR | 2 BA | Sleeps 10 | Quick View

Distance to beach: 0.0 miles to Atlantic Ocean

$745

avg/night

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Key Amenities

  • Kid friendly

About this property

Incredible spot! Expansive Cape cottage on a bluff in Nauset Heights overlooking Nauset Inlet and the Atlantic with upper level deck and a private stairway down to the beach. Casual Old Cape Cod with pine panelling throughout. The main floor bedrooms consist of a large bedroom with queen bed and a second ...

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Orleans House

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2 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Snow Shore

$321

avg/night

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Key Amenities

  • Kid friendly

About this property

'Rose Cottage' is an absolutely lovely, light and bright expanded cottage located on almost an acre in the desirable Snow Shore area of East Orleans. Recently renovated with two bedroom suites and two sleeping alcoves (one of each on both levels), multiple decks and skylights to fill the spaces with natural ...

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Orleans House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.0 miles to Mayflower Point

$287

avg/night

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Key Amenities

  • Kid friendly

About this property

Chill out (now with central A/C!) and relax at this wonderful waterfront retreat located in Mayflower Point. This charming cottage offers wonderful views of Lonnie's Pond and Kent's Point. Enjoy its own path down a slope to Lonnie's River that leads out to Pleasant Bay. Perfect for boating or kayaking. ...

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Orleans House

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5 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 2 miles to Nauset Beach

$687

avg/night

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Key Amenities

  • Kid friendly

About this property

Beautiful FIVE-bedroom home with A/C and full amenities only minutes from Nauset Beach and East Orleans village! Ideal for larger gatherings and/or extended families, this meticulous, well-appointed, and beautifully decorated home offers two separate gathering spaces, two separate bedroom wings, air-conditioning, ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly

About this property

Beutiful place to relax we had the best view from the masters bedroom, we offers breakfast and bed. This its beutiful cottage house we rental vacation summers second floor includes 2 rooms with magnificent views you will and enjoy a peaceful place

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Property Type

Orleans Cottage

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3 BR | 1 BA | Sleeps 6 | Quick View

$304

avg/night

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About this property

Immaculate and beautifully renovated three bedroom home perfectly located between Orleans Main Street and Rock Harbor. The home is set back from the road and offers privacy and the charm of Cape Cod. Main level with living room, dining room, fully equipped kitchen, two bedrooms (both with TVs) and one ...

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Orleans House

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2 BR | 1 BA | Sleeps 6 | Quick View

$261

avg/night

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Key Amenities

  • Kid friendly

About this property

Sunny and cozy cottage is just 2/10 mile from Priscilla Beach in East Orleans. This charming home offers a full length back deck, living room open to kitchen with bar seating, two bedrooms and a loft. Mini-Split A/C in the living room to keep you cool on hot summer days. It's just a 5 minute stroll ...

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Property Type

Orleans Bungalow

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2 BR | 1 BA | Sleeps 4 | Quick View

$343

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly
  • Rentals by owner

About this property

Enjoy breathtaking sunsets over Cape Cod Bay from this private, direct beachfront rental on kid-friendly, Skaket Beach in Orleans. Charming 2nd floor apartment with stunning views. Living area, 2 bedrooms, 1 bath and kitchenette. Very clean, cozy & simple. Max 4 people. Sorry no pets allowed.

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Property Type

Orleans Apartment

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4 BR | 1.5 BA | Sleeps 8 | Quick View

$454

avg/night

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Key Amenities

  • Kid friendly

About this property

Wonderful one-level cottage 3/10 mile to Nauset Beach. This 4 bedroom 1.5 home is updated, immaculate and is the perfect place to make memories for years to come. Main level offers a spacious and sunny open floor plan with vaulted ceilings and a fully equipped kitchen, spacious dining area with room ...

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Property Type

Orleans House

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$379

avg/night

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Key Amenities

  • Kid friendly

About this property

Immaculate home with 2 bedrooms and a loft sleeps 6 in a private location with beautiful water views. Tastefully decorated and spotless, this home has one king and one queen bedroom on the main level and a loft space with a queen and a double bed. The main level includes a sunny fully equipped eat-in ...

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Orleans House

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2 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 3 miles to Pleasant Bay Beach

$300

avg/night

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About this property

Launch your canoe or kayaks across the street at Town Landing/Quanset Pond! This two-level 2 bedroom 1.5 bath duplex is located on three acres of private land offering a peaceful vacation retreat. This building once served as a stable but was converted into two separate condos with exceptional privacy ...

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Property Type

Orleans Condo

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3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Skaket

$329

avg/night

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Key Amenities

  • Kid friendly

About this property

Location, Location! Sweet and cozy 2-bedroom Plus bunkhouse just 2/10ths of a mile from gorgeous Skaket Beach on Cape Cod Bay. Corner lot on a quiet road with 3 ductless A/C units, new stove & refrigerator, and outdoor shower. An ideal setting for the smaller gathering just steps to the sand! Separate ...

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Property Type

Orleans House

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Orleans Vacation Rentals

Find your ideal Orleans vacation rental today

The population of this Lower Cape town swells during the summer for good reason. Orleans has easy access to so many things that people booking vacation rentals covet. We have an outstanding selection of vacation houses perfect for adventure-seeking travelers. One of the best and most underrated parts of staying in Orleans is the easy access via route 6 to Outer Cape spots like Eastham and Wellfleet, as well other Lower Cape spots like Chatham. But you don't have to leave town if you book a vacation rental in Orleans. Let's have a look...


Orleans, MA travel advice

Summer in Orleans, Massachusetts is great, regardless of where your rental is located. But perhaps better than most places, "shoulder season" (meaning Spring and early Fall) in Orleans is a treat. Most of the restaurants, shops, and boutiques in Village Center stay open during shoulder season. And the town has some great trails for walking and biking, plus the town reduces the restrictions of having dogs at the beach. So, it's easy to see why people book vacation rentals in Orleans during the summer and the surrounding shoulder season months, as well.


Activities and beaches

Get your tide chart ready because Orleans has some of the Cape's most diverse bodies of water as well as some of its best beaches. Skaket Beach and Rock Harbor sit on Cape Cod Bay -- so if book a vacation rental near here, but sure to catch a sunset!

While on the west end of town there's Nauset Beach and Mill Pond. Nauset Beach is on the south end of the Cape Cod National Seashore, which attracts travelers from around the country and the globe. Parking is $20/day the last time we checked but if buy admission to one beach on the CC National Seashore, you can visit them all without paying.

You can't miss Pleasant Bay and Little Pleasant Bay which are accessible to the east of Route 28. This is a water-lover's paradise with everything you could ever want in one place, including some diverse wildlife.

There's a great local art scene here, too. Vacationers and year round residents love the galleries dotted around Route 6A nad Main Street including Trove Art Gallery & Boutique, the Frying Pan Gallery, Left Bank Gallery, and Coastal Craft Gallery.


Outdoor attractions

Outdoor activities rule in Orleans! There's something for all vacationers in this Lower Cape town. Ever heard of renting a catboat? You can try that or rent a kayak or paddleboard to navigate Orleans's waterways. Some of the best include Cape Kayaking, Arey's Pond Boat Yard, Goose Hummuck, or Pleasant Bay Community Boating, all town favorites.

If deep-sea fishing is your idea of the perfect vacation activity, try Dragonfly Sportfishing for a a fishing charter -- hopefully you'll see striped bass or bluefin tuna!

There are boating centers, and yacht clubs in Orleans too. If you book an Orleans vacation rental, check out Blue Claw Boat Tours. Captain Rob will help you do it right with a tour from Orleans to Chatham Harbor. Definitely on our list of "musts".


Recommended food and restaurants

Many of Orleans's top restaurants are clustered just south of the rotary connecting route 6 and route 28. There is something for most travelers for sure, so here's the deal on a few of our recommendations:

Land Ho! -- first off, classic name for a pub and grub place on the Cape. This spot right on Main Street is great for a beer and for some laid back apps and main dishes. It's popular with locals and seasonal visitors staying in vacation rentals, alike. Plus, it just turned 50!

The knack is one of the first restaurants you see as you get off the Orleans rotary from Route 6. It's known for its modern airy accommodations, burgers, and lobster rolls -- or as the locals say "lobstah rolls".

If you want more of a bar scene on your vacation, try Mahoney's Atlantic Bar & Grill. It's styling but not upscale and it has a vibrant bar scene (by Cape standards!) and is a good dinner spot with a full menu.

For some people, it's not a vacation until you've had a rockin' breakfast. For that, check out the Hole-in-One on route 6A, which has great donuts and coffee. But the show here are the muffins -- mocha fudge is a must!

We're calling right now: the best coffee joint on the Cape is Sunbird -- pretty great logo too. The lunch is sneaky great (esp for families) at this local favorite. They've made a great transition during/after the pandemic too so it's easy to order online and pick up outside.

A list of restaurants in Orleans wouldn't be complete without mentioning Hot Chocolate Sparrow on Old Colony way. Its got ice cream, coffee, espresso, sweets and, um, hot chocolate for days...


Orleans vacation rentals on Cape Cod Vacation Rentals

Booking Orleans vacation cottages and homes is super easy on CapeCodVacationRentals.com. You can save significantly over booking a hotel or an inn. Plus, you'll have all the comforts and space of home in your vacation rental. Our inventory of houses in this Lower Cape town can't be beat. Happy planning!