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!

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, 305 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.

5 out of 5 average rating, 101 reviews

Home in Yarmouth Port

Fireplace · Waterfront · 2 Kings · Cozy · DogsYes

☆ Waterfront, located on private saltwater beach (with central location) ☆ Sauna (Temporarily Unavailable) ☆ Cozy fireplace (electric) ☆ 3-season patio ☆ 1% donated to Cape nonprofits ☆ 2 Kayaks & 2 Paddle boards ☆ Outdoor fire pit & charcoal grill ☆ Ample workspace ☆ Dog Friendly ☆ Washer/dryer ☆ 2 King Beds with 50" TVs in bedrooms ☆ Outdoor shower (open May through fall) ☆ Beach chairs provided ☆ Linens, all towels provided ☆ 10min from bay or ocean beach ☆ 15min MV & Nantucket ferries

4.9 out of 5 average rating, 174 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, 132 reviews

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.

4.99 out of 5 average rating, 147 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

Salt Eire | Oceanfront Beach Home

Welcome to Salt Eire. Steps to the beach for your morning walks. The sound of waves lulling you to sleep. A place for family and friends to relax and create memories. Nestled in the dunes of East Sandwich beach sits this oceanfront property (bay side) with stunning 360-degree views of Cape Cod Bay and Scorton Creek. Spend your days sunning and swimming before you return home to this comfortably appointed house. Also check out our new sister property down the road @ApresSeaCapeCod

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, 102 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, 222 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, 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.

4.95 out of 5 average rating, 261 reviews

A serene dock extends over calm waters, featuring two Adirondack chairs positioned beside vibrant potted flowers. Lush greenery frames the scene, providing a peaceful backdrop for relaxation. The setting invites guests to unwind and enjoy the tranquility of the freshwater pond.

Cottage in Eastham

The Breeze Overlooking Minister's Pond

The Breeze is a luxurious, romantic cottage by a serene freshwater pond, surrounded by vibrant gardens. Perfect for a peaceful getaway, enjoy kayaking, canoeing, and relaxing on the dock, or explore nearby trails and the Cape Cod Rail Trail with provided bikes. Unwind with evenings by the fire pit, refreshing outdoor shower, and a plush queen bed for ultimate comfort. This private oasis offers tranquility, natural beauty, and 5-star attention to detail for your perfect escape.

4.99 out of 5 average rating, 172 reviews

The cottage exterior features a charming white facade with several windows illuminated in warm light. A welcoming front porch is adorned with potted plants, and an American flag is displayed. The surrounding lawn is well-maintained, enhancing the inviting atmosphere.

Cottage in Barnstable

Beach Glass Cottage - Pond Front

Come stay at the Beach Glass Cottage! A pristine pond front, completely renovated and tastefully decorated, 3 bedroom, 2 bathroom cottage in the heart of Hyannis. Truly the perfect get-a-way for family and friends. The Beach Glass Cottage is tucked away from the action, but within walking distance to Main Street Hyannis, which features eclectic shops, restaurants, bars, ice cream with mini golf and the Cape Cod Melody Tent is a short walk from the cottage as well.

4.88 out of 5 average rating, 464 reviews

A bright and airy interior space features a light wood table accompanied by two chairs. A comfortable gray sofa is positioned nearby, with decorative cushions adding a touch of color. Large windows allow natural light to fill the room, enhancing a cozy atmosphere.

Cottage in South Dennis

Waterfront Cottage on White Pond(Graham Cracker)

Our cottage (Graham Cracker House) sits steps from crystal clear White Pond. The cottage offers private access to the pond for swimming, fishing and boating. The large outdoor space is great for dining and relaxing by the pond. It is 1.5 miles to the Cape Cod rail trail (bike trail), close to many dining options and 3 miles to some of the best beaches Cape Cod has to offer. There is another cottage on the property for rent that sleep 4 guests. No sharks here!

Popular amenities for waterfront rentals in Orleans

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

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.

4.94 out of 5 average rating, 18 reviews

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

4.95 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

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.

4.95 out of 5 average rating, 21 reviews

Stunning West End Waterfront Views with Parking

The beach-front property is showcased with multiple levels and modern design features. The structure is surrounded by soft sandy beach and grassland, with the historic tower visible in the background under a clear blue sky.

5 out of 5 average rating, 10 reviews

PTown’s Best /on the beach + parking

4.7 out of 5 average rating, 138 reviews

An open studio cottage features wood-paneled walls and a high vaulted ceiling. A cozy bed is positioned next to a comfortable sofa, while a dining table is set for four. Natural light flows through large windows, enhancing the inviting ambiance.

Flat in Harwich Port

Cape Cod beachfront Studio cottage

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.

4.98 out of 5 average rating, 100 reviews

Waterfront with Views & Kitchen-Preston Cross Hall

5 out of 5 average rating, 7 reviews

A paved outdoor seating area is visible with several round tables and chairs arranged to provide views of the water at sunset. The sky features warm hues of orange and purple as the sun dips below the horizon, with the ocean beyond and neighboring houses in the background.

Flat in Dennis Port

Steps to the Beach & Heated Pool!

Waterfront house rentals

5 out of 5 average rating, 339 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

5 out of 5 average rating, 223 reviews

A historic home features classic New England architecture, with a peaked roof and wooden shingle siding. White trim outlines the windows and door, while a white picket fence surrounds the property. Lush greenery and colorful flowers enhance the welcoming exterior under a clear blue sky.

Home in Sandwich

Quintessential Waterfront Historic Cottage

5 out of 5 average rating, 18 reviews

Home in East Dennis

Golf simulator, Sauna, Hot Tub, mayflower beach

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

4.97 out of 5 average rating, 108 reviews

An aerial view captures a spacious lakefront home surrounded by lush greenery, with calm waters reflecting the sky. A vast lawn leads to the edge of Lawrence Pond, providing a serene backdrop to the property.

Home in Sandwich

Serene Lakefront Escape on Cape Cod

4.9 out of 5 average rating, 200 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

4.98 out of 5 average rating, 42 reviews

A serene view of a freshwater pond is captured, with gentle ripples reflecting the clear blue sky. Leafless trees frame the scene, adding a touch of nature's beauty. Lush greenery can be seen in the distance, showcasing the peaceful surroundings.

Home in North Eastham

Cozy Cape Stay! bike path, beaches, water view!

5 out of 5 average rating, 49 reviews

A charming beachfront cottage features a light gray exterior, complemented by bright white trim and multiple window panes. Lush green shrubs frame the front walkway, which is made of stone and brick. The inviting entrance is accentuated by a blue door and a lantern light fixture.

Home in New Seabury

Cape Cod Beachfront Cottage

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!

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

4.93 out of 5 average rating, 44 reviews

A light-filled living area features a cozy sofa layered with a soft throw, accompanied by a stylish coffee table. The calming wall art depicts ocean waves, while lamps provide additional lighting. A door leads outside, and a chair adds a pop of color.

Apartment in West Dennis

1BR 2nd Floor Condo with pool

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, 109 reviews

Modern Beachfront Condo, Great Views and Location!

4.96 out of 5 average rating, 95 reviews

The living area features a light-colored sofa paired with matching armchairs. A small table holds fresh flowers. Soft lighting from lamps creates a comfortable environment. Large sliding doors provide natural light and open to an outdoor patio with a dining set.

Apartment in Brewster

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access

5 out of 5 average rating, 88 reviews

An open living area features large glass doors that provide views of the golf course. A comfortable seating arrangement includes a recliner and a sectional sofa. A spiral staircase leads to the loft above, and a mounted television is positioned above a modern fireplace.

Apartment in Brewster

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

A serene waterfront view captures the calm bay under a clear blue sky. The foreground features a well-maintained lawn with stone pathways leading to lounge chairs and umbrellas on a sandy area, providing direct access to the water.

4.95 out of 5 average rating, 208 reviews

Bayshore 9 Waterfront Renovated Condo with Parking

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.