Waterfront holiday rentals in Orleans

Cottage in South Yarmouth

A serene waterfront view showcases a tranquil pond surrounded by lush greenery. Two kayaks are visible on the grassy area, while the deck features a wooden table with white chairs, inviting relaxation and outdoor dining.

5 out of 5 average rating, 241 reviews

SerenityViews | Waterfront | King Bed | Kayaks SUP

Enjoy our cottage's charm and comfort with panoramic views and abundant sunlight. Comfortably hosts 2 families. Wake up to incredible sunrises. Lounge on the hammock or swim/fish/kayak in our beautiful backyard waterfront Long Pond. Explore the Cape in each direction: beautiful beaches and endless fun activities/interests. At the end of the day, enjoy dining on the deck as you grill. Sit back on the patio with a cocktail and gaze at the star filled sky and ambiance from the fire table. Welcome!

5 out of 5 average rating, 184 reviews

Home in South Yarmouth

King Beds * Sauna *Bar Shed * Netflix&HULU&ESPN

Cape Away is a cozy, and entertainment focused family & pet friendly retreat in the charming Mid-Cape region. Start your mornings with coffee in the fully stocked kitchen, hit up nearby beaches, then unwind in the sauna, outdoor shower, or by the fire. With games, private fenced backyard, shed bar and fast WiFi, you’re 5–10 minutes from top restaurants and beaches. We included unlimited Disney+, Hulu, ESPN, Netflix and PrimeVideo for all guests! Book now and make your Cape Cod memories here.

4.96 out of 5 average rating, 140 reviews

Two kayaks are stored beside a shed in a natural setting, surrounded by tall grass. A view of the calm water reflects the greenery of the area, while a cozy indoor space showcases a gas fireplace and comfortable furnishings.

Cottage in South Dennis

Local Beach+ Fireplace + Hot Tub Under the *Stars*

Welcome to the Bayside Retreat! Enjoy the real Cape Cod in this Quintessential Beach Rental Featuring: Private hot tub, outdoor patio & sofa set in a peaceful backyard 🕊️ 2️⃣ Kayaks- Outdoor Shower- Gas Grill 🔥 Indoor Gas Fireplace ❄️ Mini Splits ✔️Games ✔️Washer/Dryer 📺 55” Sony TV w/ Apps & DirectTV 🛋️ Comfy Furnishings➕Stocked Kitchen Watch the birds, relax out back in peace & privacy or go explore! 📍 Centrally located ❌ NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

4.78 out of 5 average rating, 153 reviews

A contemporary cape-style home is framed by lush greenery and tall trees, set back from a sandy path leading to the entrance. The home features a charming front porch with large windows, offering a welcoming presence amidst the tranquil outdoor surroundings.

Home in Eastham

Contemporary Cape, Marsh/Bird Sanctuary views, AC!

Unwind in paradise! This stunning property offers the best of both worlds: refreshing breezes from the marsh through open windows and doors, and newly installed Air Conditioning for rare, scorching days. Wake up to sunrises, a symphony of birds, the endangered Osprey, Great Blue Heron, and Egrets outside your window. Audubon is across the marsh. At night, owls, moonrise, and stars!! A bright, airy oasis on a quiet cul-de-sac, minutes from the beach, shopping, and scenic bike/rail trail.

A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.

4.95 out of 5 average rating, 299 reviews

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

4.9 out of 5 average rating, 172 reviews

An outdoor deck extends over panoramic views of the waterfront, featuring a dining table with dark wood chairs shaded by a green umbrella. The deck is surrounded by lush greenery and offers ample space for relaxation and dining, enhancing the outdoor experience.

Cottage in Wellfleet

Cape Cod Spectacular Waterfront Cottage

Welcome to our internationally acclaimed and regionally featured cottage located on Lieutenant Island in Wellfleet, MA. It's in a private location with panoramic views and a western exposure featuring beautiful sunsets nightly (weather permitting)! TripAdvisor internationally featured property in July, 2015: Bostondotcom in July, 2016: Business Week in July, 2020. Please contact us for nightly, weekly or long term quotes or discounts. Pricing and lengths of stay are subject to change.

4.95 out of 5 average rating, 128 reviews

An aerial view captures a serene pond surrounded by lush greenery. Clear blue water reflects the sky, while sandy areas and aquatic plants line the edges. The tranquil environment suggests opportunities for relaxation and connection with nature.

Guest house in Brewster

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.

A charming beach house with shingle-style siding is displayed, set within a landscaped yard. Two large bushes frame the entryway, and the building features multiple rooflines and skylights. A brick pathway leads to the front door, with trees providing partial shade in the foreground.

4.96 out of 5 average rating, 101 reviews

Beachfront Charmer! Newly Renovated.

Steps to a beautiful sandy beach and just a mile to the heart of Chatham! This charming, newly renovated beach house has the amenities you need to make the most of your time with friends & family. Just 300 ft from Little Beach & a 5 minute walk to Chatham Lighthouse and Lighthouse Beach, we've made our new home the perfect place to gather and relax. All BRs and Living room have AC. Grill on the back deck, stroll to town, rinse off in the outdoor shower...this house has it all!

4.96 out of 5 average rating, 219 reviews

A tranquil scene captures a couple seated on a dock, surrounded by tall green grasses. The calm water reflects soft hues of pink and blue from the sunset, creating a serene backdrop of trees across the pond.

Home in Dennis Port

Lakefront House/Private Dock/Year Round Hot Tub/AC

Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.

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.

4.97 out of 5 average rating, 157 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.

4.86 out of 5 average rating, 567 reviews

An open living area features a comfortable gray sofa facing a round dining table and chairs. A full kitchen is equipped with modern appliances, including a stainless steel refrigerator. Natural light brightens the space through large windows, complemented by light-colored wooden flooring.

Cottage in South Dennis

Beachfront Cottage on White Pond (Marshmallow)

Our Cottage sits directly on White Pond tucked away on acres of private property. Our cottage offers a private beach, deck, outdoor shower, outdoor dining area all while enjoying Cape Cod. White Pond is ideal for swimming, boating and fishing. The bike path and well known beaches are less than 2 miles and near to many delicious restaurants. There is another cottage on this property that sleeps four if you have other guest wanting to join

4.96 out of 5 average rating, 129 reviews

A serene beach scene is captured, featuring calm waters reflecting a clear blue sky. Grass and low vegetation frame the foreground, leading to gently sloping sandy shores. In the distance, the outline of an island is visible against the horizon, contributing to the tranquil atmosphere.

Bungalow in Wellfleet

Beach Bungalow - Cape Cod Classic

Artwork, Antiques, Beach, Backyard, Privacy This cottage has everything you can imagine and more. Well stocked and maintained. Cape Cod charm and modern amenities. Responsive owner and close to everything - town, harbor, restaurants, park, and of course Mayo Beach footsteps away. Next-door is Beach Bungalow #2 - see link below. airbnb.com/h/beachbungalow2 “Copy/paste link above to your browser.”

Popular amenities for waterfront rentals in Orleans

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.94 out of 5 average rating, 18 reviews

An outdoor deck area features a small table with two chairs, surrounded by flowering plants. The sliding glass door provides access to the interior, where natural light can be seen. The deck flooring is composed of wooden boards, enhancing the inviting nature of the space.

Flat in Provincetown

Wonderful in-town beach/studio! Steps to action!

4.98 out of 5 average rating, 123 reviews

A bright living area features a large window that allows natural light to fill the space. Comfortable seating includes a gray sofa and a dark blue loveseat. A wooden coffee table sits between them, and a ceiling fan helps maintain a comfortable temperature.

Flat in Sagamore

Cape Cod Canal Home

4.81 out of 5 average rating, 110 reviews

A charming cottage is nestled against sandy dunes, featuring a covered porch with seating. The exterior showcases light grey shingles, and a large circular decorative element is centered on one wall. Beach chairs are positioned near the entrance, inviting relaxation with ocean views.

Flat in Harwich Port

Cape Cod Beachfront 2 bedroom Cottage Harwich

4.93 out of 5 average rating, 210 reviews

Flat in Eastham

The Lotus-Hot Tub/Kayaks/Ebikes/Waterfront

4.95 out of 5 average rating, 19 reviews

A spacious deck overlooking a serene water view features outdoor seating with a comfortable wicker sofa and round tables. The railing is white, and the surroundings consist of lush greenery and a clear blue sky with scattered clouds.

Flat in West Yarmouth

Waterfront Oasis in Yarmouth, Cape Cod

4.95 out of 5 average rating, 19 reviews

A shared waterfront deck features comfortable seating arranged around a glass-top table, with a panoramic view of the Bay during sunset. The horizon displays a blend of orange, pink, and blue hues, while trees frame the scene, adding depth to the serene coastal environment.

Flat in Provincetown

Stunning West End Waterfront Views with Parking

4.98 out of 5 average rating, 100 reviews

A bright, open living space features large windows that allow natural light to fill the room. A comfortable couch with decorative pillows sits alongside a classic wooden chair. Brick and wood beams contribute to the rustic charm, complemented by original artwork on the walls.

Flat in Provincetown

Waterfront with Views & Kitchen-Preston Cross Hall

Superhost

An aerial view captures a serene kettle pond surrounded by lush greenery, with homes positioned thoughtfully around it. A circular road is visible, enhancing the peaceful, residential atmosphere of the neighborhood.

Flat in Cotuit

4.91 out of 5 average rating, 11 reviews

2 BR pond suite w/ private kitchen/bath/living

Waterfront house rentals

5 out of 5 average rating, 336 reviews

A wooden outdoor table and benches are positioned on a stone patio, overlooking a serene pond. Lush greenery lines the water's edge, and white flowers in a planter enhance the natural setting. The calm water reflects the surrounding trees and sky.

Home in West Yarmouth

gorgeous waterfront cottage w/4kayaks and 2 SUPs

4.96 out of 5 average rating, 68 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

4.97 out of 5 average rating, 29 reviews

An outdoor seating area is covered by a gazebo, featuring plush blue cushions on woven furniture. A fire pit table sits at the center, with flames providing warmth. Beyond the seating, a fenced-in lawn creates a private retreat, complemented by a storage shed.

Home in Dennis Port

3-min walk to BEACH! Private luxury Backyard!

5 out of 5 average rating, 94 reviews

Home in Yarmouth Port

Sauna · Fireplace · Waterfront · 2 Kings · DogsYes

4.99 out of 5 average rating, 146 reviews

The exterior of a spacious coastal property is shown, featuring a wraparound porch and light grey shingle siding. A clear blue sky complements the beach setting, with soft sand leading to the ocean in the background. Lush greenery borders the property, providing a sense of seclusion.

Home in East Sandwich

*Oceanfront Beach Home*

A calm freshwater pond is surrounded by lush greenery and tall trees. A float is visible on the water, providing a serene spot for relaxation. Lilypads are scattered across the surface, reflecting the clear blue sky.

4.92 out of 5 average rating, 95 reviews

Spacious studio on lovely pond in Chatham

4.9 out of 5 average rating, 147 reviews

A heated indoor pool is framed by sleek gray walls and illuminated with recessed lighting. Large sliding glass doors offer a view of the outdoor patio. Colorful pool floats and equipment are neatly arranged nearby, providing options for leisure activities.

Home in Plymouth

Seaview Summit | Ocean Views, Indoor Pool, Beach

4.89 out of 5 average rating, 198 reviews

A charming cottage is surrounded by lush greenery and soft landscaping. The exterior features a light wood shingle design with a welcoming porch and a shaded deck area. Outdoor seating is present, inviting relaxation under the clear blue sky.

Home in Hyannis Port

Cottage with private beach in Hyannis Port

Waterfront apartment rentals

A scenic view showcasing the bay with gently rippling waters and distant land on the horizon. The foreground features coastal vegetation, including pines and shrubs, along a wooden pathway leading toward the beach. Nearby, a stop sign indicates road access.

4.97 out of 5 average rating, 240 reviews

P-Town Beach Beauty on the Bay. Water View!

Superhost

A serene waterfront view displays calm waters under a clear blue sky. A private beach area is visible with deck chairs and umbrellas arranged neatly on a sandy spot. Lush green gardens and a winding stone path add to the natural beauty of the setting.

4.84 out of 5 average rating, 111 reviews

Bayshore11 Waterfront Renovated Condo with parking

The tranquil waters of the harbor are seen, dotted with various boats gently bobbing on the surface. A barrier of rocks outlines the marina, while the calm blue of the water reflects the soft light of the sky.

4.93 out of 5 average rating, 352 reviews

Beachfront Town Center

A bright living space features large windows providing views of the waterfront. A white sofa and a cozy sitting area surround a circular coffee table. A patterned area rug anchors the space, while light filters in, enhancing the serene atmosphere.

4.99 out of 5 average rating, 108 reviews

Modern Beachfront Condo, Great Views and Location!

4.87 out of 5 average rating, 118 reviews

An open-concept living area features a spacious blue sectional sofa and a flat-screen TV mounted on the wall. Natural light floods the room through large windows, offering views of the surrounding greenery. A decorative plant and a textured area rug add warmth to the space.

Apartment in Chatham

Steps to Private Beach in Chatham

A view through a clean window reveals sandy beach and ocean. Soft clouds float in the sky over the water, with scattered trees visible along the shoreline. Kayaks are positioned on the sand, adding a touch of color to the natural setting.

4.96 out of 5 average rating, 50 reviews

Meant 2B

4.85 out of 5 average rating, 61 reviews

A wooden sign is displayed on a light-colored wall, featuring the phrase 'Heaven is a little closer by the Beach' in white lettering on a teal background. The sign is framed in a rustic white border, enhancing its coastal charm.

Apartment in West Dennis

Hidden Hideaway

A spacious dining area is presented with a modern table surrounded by six white chairs. Natural light enters through multiple windows, illuminating the comfortable gray sofa and sleek entertainment unit in the background, which features a minimalist fireplace.