House holiday rentals in Orleans

The private yard features a fire pit surrounded by blue chairs, with a small patio table and umbrella nearby. Lush greenery and flowering plants line the path, leading to the entrance of the cottage, while a wooden fence provides a sense of seclusion.

4.96 out of 5 average rating, 25 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.

An outdoor gathering area is arranged around a circular fire pit, with several comfortable chairs and accent tables. The surrounding garden is filled with lush greenery and vibrant blue hydrangeas. Soft lighting enhances the cozy ambiance as twilight descends.

4.99 out of 5 average rating, 96 reviews

Modern Cape Escape Retreat- Walk to Pilgrim Lake

➤ Relax by the Outdoor Fire, stay in for a Family Movie Night, or explore Orleans’ nearby Beaches/Shopping/Dining ➤ Central: ★ Walk to Pilgrim Lake ★ 5mins drive to Beaches/Shopping ➤ Nestled in the peaceful windswept woodlands of the Lower Cape, this bright & spacious home is the ideal place for calm, connection & conversation ➤ A favorite of Family Holidays, Friends groups & Freelancers, this recently-renovated Orleans acreage transports you to a simpler time-where stress is left behind.

An aerial view captures a cottage nestled among vibrant green trees, showcasing the surrounding natural landscape. A glimpse of the ocean is visible in the distance. The cottage features a deck facing the woods, providing a serene and secluded ambiance.

5 out of 5 average rating, 28 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.

4.9 out of 5 average rating, 101 reviews

The exterior of a classic Cape Cod house is shown, featuring shingle siding and multiple large windows. The surrounding landscape includes manicured shrubs and a gravel driveway, alongside a tree-lined backdrop that provides a natural setting. The entrance, framed by steps, leads to the welcoming front door.

Home in North Eastham

Large, Cozy, Walk to beach, Central AC, Game room

This classic, large Cape Cod house is just perfect for friends or a family reunion. The beautiful Thumpertown Beach is 0.3 miles or a 5-10 min slow stroll down the street. The house is large enough to accommodate everyone comfortably and has a convenient layout that also provides plenty of privacy. There is central A/C that covers the entire house, all rooms have hardwood floors, newer beds, comfortable mattresses and quality pillows. New 18x24 deck has Polywood furniture and Weber gas grill.

4.96 out of 5 average rating, 194 reviews

The exterior of a charming two-story home is presented, featuring a sloped roof and light blue shutters. Well-maintained greenery surrounds the entrance, which is framed by a modest walkway and bordered by vibrant hydrangeas. A fenced yard offers a sense of privacy.

Home in Dennis Port

4 Minute Walk to Beach, Cape Cod Serenity

Located on a quiet corner with lots of privacy, 2 full baths, 4 bedrooms, outdoor shower, and a quick stroll to the beach. Activities, great restaurants and shopping are moments away! Fully equipped kitchen, linens included, outdoor seating, a grill and beach accessories will make your trip great. 1 full bath down with two bedrooms, 1 full bath up with two bedrooms. AC/Heating units installed to make your stay more enjoyable! June, July and Aug are 7 day stays w/ Friday as arrival day!

The exterior of the home showcases a charming coastal design, featuring white siding and blue shutters. A neatly landscaped front yard contains low hedges and fresh mulch, with stone pathways leading to the entrance. Solar panels are visible on the roof, emphasizing eco-friendly features.

4.89 out of 5 average rating, 9 reviews

Gorgeous Coastal Escape! 5BR w Hot Tub + Bikes!

Orleans Holiday House is a modern coastal Cape Cod beach retreat in Orleans, MA, with 2 living rooms, a game room, a private hot tub, a hot/cold outdoor shower, a fire pit, and a pergola patio. Sleeps up to 10 in 5 bedrooms. 5 minutes to Skaket Beach sunsets, 7 minutes to Nauset Beach and the Cape Cod National Seashore, and about 7 minutes to Rock Harbor. Stocked chef’s kitchen, A/C, Wi-Fi, complimentary video games, bikes, beach gear, baby gear. Steps from Eldredge Park and the Rail Trail.

5 out of 5 average rating, 26 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.

4.9 out of 5 average rating, 253 reviews

A cozy living area is presented with light-colored walls and wooden floors. Comfortable seating includes two upholstered chairs and a sofa with a neutral cover. A coffee table sits in front, and the open kitchen is visible in the background, enhancing the space's inviting nature.

Home in Truro

Cape Cod Getaway 2 Bedroom Cozy Home

Newly updated in March 2023 with new white interior paint, new black doorknobs and cabinet pulls and new blinds throughout the home. Fresh paint, updated hardware, some new small appliances and added new art but same Cape cottage charm! NOTE: Weekly rentals mid-June through mid-September- Linens and towels can be provided in a basket or you are welcome to bring yours from home- just let us know. During this time (Mid June through Mid September, check in and out are on Saturdays.

A charming cottage is set amidst well-maintained landscaping, featuring shingle siding and a welcoming front porch. Natural light is evident in the multiple windows, and the property is enclosed by neatly trimmed hedges, offering privacy and a cozy atmosphere.

5 out of 5 average rating, 77 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.

4.96 out of 5 average rating, 194 reviews

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

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.

4.87 out of 5 average rating, 121 reviews

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

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!

A spacious backyard is surrounded by trees and features a well-maintained lawn. The house is visible in the background, with a light-colored exterior and multiple windows. A hammock is suspended between two trees, creating a relaxed outdoor space.

4.92 out of 5 average rating, 26 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.

Popular amenities for house rentals in Orleans

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The backyard features an inground pool illuminated at night, surrounded by wooden decking. Nearby, a shed with white shutters enhances the outdoor space, while lush greenery provides a serene backdrop.

4.91 out of 5 average rating, 33 reviews

5-bedroom Cape with a pool and yard games.

4.88 out of 5 average rating, 17 reviews

A dining area features a large wooden table surrounded by eight chairs, positioned on a soft area rug. Natural light filters through the sliding glass doors, enhancing the space that opens to the kitchen, which is equipped with modern appliances and ample cabinetry.

Home in East Dennis

Family Fun- Games, Pool & HotTub, Dogs ok! Slps 10

5 out of 5 average rating, 19 reviews

A modern home with light grey siding is featured in the background, surrounded by landscaped gardens. A heated saltwater pool, with clear blue water, is framed by grey stone paving. Lounge chairs and shaded seating are situated beside the pool, enhancing the outdoor space.

Home in Popponesset

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

4.88 out of 5 average rating, 25 reviews

An aerial view of a spacious backyard features a heated pool surrounded by a grey stone patio. Lounge chairs and umbrellas are positioned around the pool. The house showcases multiple large windows and a deck, with green grass and trees creating a private setting.

Home in Plymouth

Mansion with Heated Pool Near Ocean

4.94 out of 5 average rating, 71 reviews

A bright studio unit features a queen-sized bed with a comfortable pull-out sofa nearby. Natural light floods the space through large windows. A small dining table with two chairs is positioned next to the seating area, providing a functional living space.

Home in Dennis Port

Walk to the beach or sit poolside! Updated studio!

4.9 out of 5 average rating, 63 reviews

The exterior of a multi-level home is shown, featuring large windows and a wrap-around deck. A screened porch is visible on the lower level, while manicured grass surrounds the structure. The sky is clear, providing ample natural light to the setting.

Home in Dennis

Cape Cod Lakefront Home

4.95 out of 5 average rating, 20 reviews

Home in East Sandwich

Coastal Retreat in Sandwich -Pool Access, Dogs OK!

5 out of 5 average rating, 3 reviews

Home in North Eastham

Game Room- Movie Projector- Holiday Heaven

Weekly house rentals

A historic two-story Cape Cod home is surrounded by lush greenery and well-maintained landscaping. The exterior features a combination of dark wooden siding and classic shutters, with a welcoming front porch and neatly trimmed bushes flanking the entrance.

5 out of 5 average rating, 6 reviews

The Cape Escape

5 out of 5 average rating, 6 reviews

A warm bedroom features vaulted wooden ceilings with exposed beams. A spacious bed is adorned with light-colored bedding, and a fireplace is located nearby. A desk with a chair is positioned beside a sliding glass door that opens to a balcony, allowing for natural light and scenic views.

Home in Harwich

Lakeside Retreat in Pleasant Lake

4.96 out of 5 average rating, 70 reviews

An outdoor seating area is presented with plush, striped furniture and a large firepit at the center. A bright turquoise umbrella provides shade, while the tranquil waterfront view showcases shimmering water and greenery. Potted flowers add a touch of color to the serene setting.

Home in Harwich

Waterfront★ Pvt Beach ★ On Bike Path ★Bikes★Kayaks

A two-story gray house is framed by trees and features large windows allowing natural light to fill the space. In the foreground, four colorful Adirondack chairs in blue and green are arranged on a grassy area, inviting relaxation outdoors.

4.97 out of 5 average rating, 33 reviews

Orleans Pleasant Bay CulDeSac 4BR 2BA

5 out of 5 average rating, 22 reviews

A cozy exterior view of the house features a gravel driveway leading up to a classic Cape Cod cottage. Lush green lawns are complemented by well-maintained gardens and tall trees. The house is set back from the street, with a spacious fenced-in yard enhancing privacy.

Home in Dennis Port

Cottage Oasis by Lake-Kayaks, Fire Pit & Huge Yard

A spacious yard is framed by lush trees, featuring a stone patio with white outdoor chairs surrounding a fire pit. The historic farmhouse is visible in the background, complemented by a sunny patio area with umbrellas for shade.

5 out of 5 average rating, 31 reviews

Spacious home_Fenced-in yard_Pets considered

4.88 out of 5 average rating, 8 reviews

The image captures a scenic shoreline with gentle waves lapping against the grass-lined bank. A meandering waterway leads into the distance, bordered by trees and quiet cottages. Soft blue skies are present overhead, enhancing the calm environment and natural beauty of the coastal landscape.

Home in Eastham

Eastham Bungalow

4.96 out of 5 average rating, 28 reviews

The exterior of a charming beach cottage features weathered cedar shake siding and well-maintained landscaping. A welcoming pathway leads to the entry door, flanked by two sets of windows adorned with flower boxes. The lawn is landscaped with shrubs and mulch.

Home in Chatham

Charming Chatham Cottage

Private house rentals

4.93 out of 5 average rating, 27 reviews

A charming two-story house is positioned on a well-maintained lawn. The exterior features light siding with navy blue shutters and a welcoming front door. Two blue Adirondack chairs are placed in front, surrounded by neatly trimmed bushes and a gravel pathway leading to the driveway.

Home in Chatham

Amazing Location! Chatham Center, Walk to Beach!

5 out of 5 average rating, 7 reviews

Home in Harwich

The Hideaway - Harwich Port Getaway

5 out of 5 average rating, 56 reviews

Home in South Dennis

Family Retreat in the Heart of Cape Cod!

The exterior of a classic Cape-style house is showcased, featuring a well-maintained pathway of brick leading to the entrance. Lush greenery surrounds the home, complemented by colorful blooming flowers, including vibrant red azaleas.

4.8 out of 5 average rating, 5 reviews

Beach Road pearl. 1 mile to Nauset Beach

4.98 out of 5 average rating, 148 reviews

A sandy beach is lined with beachgoers enjoying the sun, and colorful umbrellas provide shade. Gentle waves ripple in the water under a clear blue sky, while grassy dunes frame the scene, highlighting the natural beauty of the coastal location.

Home in North Eastham

Private Bay Beach and Sunset Views! Dog friendly.

5 out of 5 average rating, 11 reviews

Home in Brewster

Walk to Beach, Bike path and Nickerson state park

4.92 out of 5 average rating, 49 reviews

A contemporary Cape home is positioned on a spacious grassy lot. The exterior features a shingled roof, classic front door with decorative trim, and symmetrically placed windows. Mature trees and landscaped shrubs surround the house, enhancing the private feel of the cul-de-sac setting.

Home in Eastham

Beautiful Private Eastham Cape! Central to all!