Holiday houses in Dennis Port

4.98 out of 5 average rating, 103 reviews

A backyard space is equipped with a fire pit surrounded by four white Adirondack chairs, providing a cozy gathering area. String lights hang overhead, illuminating the outdoor dining table set for a meal. A charming cottage is visible in the background, enhancing the inviting atmosphere.

Home in West Dennis

Sunset Sabbatical Cape Cod

**Newly updated Bathroom for 2026 Season!** Put your feet up and enjoy yourself! Just a 5 minute walk to South Village Beach, you will enjoy everything Cape Cod has to offer. A backyard oasis, complete with Outdoor Shower, beautiful lights, fire pit and grill - you will create family memories here for a lifetime. Updated kitchen with new gas stove, dishwasher and microwave. High-speed WiFi, Roku TVs, luxury pottery barn linens & towels. Small Hypoallergenic Dog(s) allowed with a $50 pet fee.

LocationFamilyBiking

The living area features a cozy arrangement of blue sofas surrounding a coffee table, with artwork on the walls and soft lighting. A fire pit shines brightly in the backyard, where guests gather under string lights, creating a welcoming atmosphere. A spacious bedroom includes a neatly made bed with beach-themed decor and a fan overhead. A storage area displays bicycles, demonstrating available amenities for outdoor activities.

4.92 out of 5 average rating, 425 reviews

★ 0.4mi Beach &Village ★Firepit & Fireplace★ Bikes

✅4 adult bikes / helmets / beach chairs ✅Woodburning FPL in LR w/65” ROKU TV ✅Located at end private cul-de-sac, 0.4mi to ocean beach & 1/2mi to Village ✅Steps to restaurants & Sundae School Ice-Cream ✅Enjoy the backyard w/plenty of seating, fire-pit, outdoor shower & hammock ✅Large eat-in kitchen w/Island ✅2 Queen BR’s downstairs & 2 twin + rollaway in loft plus 1/2 bath ✅Pet Fee $30/day ✅1200 Mbps FastWiFi ✅Washer/Dryer ✅ Full A/C ✅All linens included & beds made Locally managed

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A charming beach cottage is shown with a wooden exterior and a front porch adorned with string lights. An American flag is displayed on the porch. A fire pit area with seating is visible on the lawn, surrounded by gravel and greenery.

4.96 out of 5 average rating, 51 reviews

Cape Escape - Steps to Beach & Pelham House

Welcome to your dream Cape Cod beach vacation: a newly renovated beach cottage, situated just an easy two-minute walk to your semi-private smaller beach and a 5-minute walk to the larger popular Sea Street Beach. Your beach house features three comfortable, airy, and bright bedrooms, including two queen beds and two twin beds. The home providing ample sleeping space for up to six guests. You'll even find a twin daybed on the window wrapped front porch to lounge on after a long day in the sun.

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A cozy living room features a large, light-colored sectional sofa adorned with various decorative pillows. A neutral coffee table sits centrally on a woven area rug. Natural light enters through multiple windows, and a wall-mounted flat-screen TV is visible, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 301 reviews

Walk to Beach - Experience Dennis Beach House - AC

A quaint, cozy, well-decorated & well-equipped Cape Cod cottage located .2 miles away from Sea St Beach and a variety of other bars/restaurants, coffee shops and more. The house sleeps 5 people comfortably and has 1 small bathroom. Kitchen is fully stocked. 4-6 bath towels will be provided. The house has many smart home tech amenities, central air, Temperpedic mattresses, and a lovely & large outdoor space/back deck. First time booking on Airbnb? Save using link: www.airbnb.com/c/brianm30025

LocationFamilyBarbecue

4.97 out of 5 average rating, 301 reviews

Pet Friendly - Walk to Downtown Dennis Port!

Newly renovated - cozy, clean and bright! PET FRIENDLY! (PRE APPROVAL required) All amenities provided for an enjoyable and relaxing family vacation or quick get-a-way! Three car driveway and private outdoor shower. Five minute walk to Dennis Port Main Street shopping, restaurants, yoga, Pet Salon, and Town playground. South Side Beaches and Ponds just 1 mile away as well as Cape Cod Bike Trail minutes away! Pet friendly beaches in Dennis after Labor Day and before Memorial Day weekends.

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A spacious living area is presented with large windows offering panoramic views of the lake. A comfortable sectional sofa and inviting armchairs surround a coffee table, with light wood flooring and a neutral rug enhancing the relaxed ambiance. The fireplace is styled neatly, with decorative elements arranged nearby.

4.97 out of 5 average rating, 39 reviews

Stunning Waterfront Home w/ Hot Tub, Deck & Office

Stunning lake views from almost every room! This newly remodeled home sits right on beautiful Swan Lake & offers direct water access. Kayak, paddle board or fish right from the backyard. Wake up and enjoy your morning coffee on the deck off of the master bedroom or a cocktail on the other deck connected to the Office, watching the sun set over the lake. Hot tub, outdoor shower, grill & fire pits. Minutes from restaurants, shopping & beaches. Next to the Cape Cod Rail Trail for biking.

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4.93 out of 5 average rating, 106 reviews

Oceanview Cottage, Million $ View Sea Street Beach

Oceanview Cottage! Everything you will need for your Cape Cod stay including the best view. Wake up to the scent of the ocean, see and hear the waves, make your way down to the sand to sink your toes right in. We have fully updated everything in this home. Newer furnishings, including a full kitchen, bath, central AC, outdoor shower for your stay! You won't believe your eyes and the changes we made! Cape Cod decor, homey, and warm! Quick stroll to The Pelham Rooftop Restaurant!

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5.0 out of 5 average rating, 12 reviews

Luxury Waterfront - Hot Tub, Deck & Waterviews

Welcome to Aunt Laura’s Retreat, a newly renovated waterfront home ideal for families and groups seeking a relaxing Cape Cod getaway. Enjoy beautiful water views from every room, direct access to Swan Pond for kayaking and beautiful sunsets to end the day. Unwind in the hot tub, dine on the deck overlooking the water, or relax on the lower patio with a grill and cozy seating. - Direct access to Swan Pond - 5 min drive to Sea Street Beach - Close to Cape Cod Rail Trail & dining

LocationFamilySleep quality

4.94 out of 5 average rating, 17 reviews

Newly renovated, 5 min walk to beach!

Welcome to the Captain's Cottage! This newly renovated, fully stocked, family friendly, 1960s home is less than a 5 minute walk to Haigis Beach and under a mile from many famous restaurants and shops. The home exudes that Old Cape style, yet still provides modern amenities and central air to ensure a fun filled and memorable vacation. Do not worry about packing linens/towels, beach gear, or even baby/toddler necessities - all are included with the home. Just arrive and relax!

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A charming Cape Cod house is presented, featuring a light grey exterior and a sloped roof. A white picket fence surrounds the front yard, adorned with neatly trimmed bushes. A stone pathway leads to the front door, framed by windows and a symmetrical layout.

4.86 out of 5 average rating, 229 reviews

Lovely! 4Bed 3baths Walk to Beach DennisPort

Dennisport! Excellent location! Great for groups and families! Easy walk to 3 public Beaches with the warm waters of Nantucket sound! This lovely home is fully equipped, comfortably sleeps 8 with 4 bedrooms, 3 baths, outdoor shower and al fresco dining on deck or porch. A mile to downtown where you'll find great restaurants and cafes. The space is designed for comfort and convenience and exploring the Cape from this Dennisport home is easy due to it's central location.

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4.96 out of 5 average rating, 28 reviews

3 bedroom Cape Escape!

Have fun with the whole family at our newly renovated cottage. This relaxing 3BR/1BA house is walking distance to wonderful restaurants & shops. Only a .8 mile walk to the beach. Enjoy a private fenced in backyard, patio, firepit, & outdoor shower. Sleeps 5. The house is stocked with bath & beach towels as well as a fully stocked kitchen with utensils, plates, cups, etc. The shed has a beach wagon, beach toys and beach chairs for guests to use.

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The exterior of a cottage is presented, featuring a welcoming front porch with a gabled roof. Pebbled white gravel surrounds the home, and flower beds with colorful blooms enhance the entrance. Soft sunlight illuminates the traditional shingle siding, with a flag displayed on the property.

4.83 out of 5 average rating, 18 reviews

New! Beach Cottage| 3 min walk to Beach| Pet Ok

Welcome to Sandy Cheeks 🐚 ☀️ 🌊 Cape Cod Beach Cottage | 3 Min Walk to Beach Welcome to your perfect beach getaway! Our newly renovated, quintessential Cape Cod cottage is packed with character, charm, and all the amenities you need for a memorable stay. Nestled in a prime location just a 3 minute walk to the beach and steps from local restaurants, shops, and cafes, this cozy retreat offers the best of both relaxation and convenience.

LocationFamilyAir conditioning

Popular amenities for Dennis Port holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Dennis Port

The living area showcases wood-paneled walls and a spacious white sofa centered on a light area rug. A coffee table sits in front, with a vase of greenery. Natural light enters through a window adorned with sheer curtains, while framed artwork decorates the walls.

4.93 out of 5 average rating, 27 reviews

The Sweet Retreat

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The main living area features an open layout with high ceilings and large windows. A comfortable sectional couch sits adjacent to a media unit with a flat-screen TV. A dining table with benches accommodates four to six people. Natural light enhances the inviting space.

4.98 out of 5 average rating, 82 reviews

Walk to beach/Pelham House, dog friendly, sleeps 6

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5.0 out of 5 average rating, 22 reviews

Dennis Port | 5-Min to Glendon Beach

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Superhost

5.0 out of 5 average rating, 3 reviews

Cozy cottage w/ backyard. Walk to beach & dining.

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The entrance of the cottage is visible, featuring a warm red exterior. Shuttered windows provide natural light, while a covered deck with seating enhances outdoor living. The beach is just beyond the railing, showcasing the cottage's proximity to the shore.

4.97 out of 5 average rating, 32 reviews

Expansive Ocean Views

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5.0 out of 5 average rating, 19 reviews

Fall Specials - Family Friendly Beach House

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A spacious backyard is featured, showcasing well-maintained green grass and a patio area. Outdoor seating options surround a grill, while vibrant blue chairs are arranged nearby a fire pit. The house is set against a backdrop of trees, providing a sense of privacy.

4.94 out of 5 average rating, 34 reviews

Relaxing West Harwich getaway!

LocationFamilyWalkability

A charming single-story house is surrounded by well-maintained gardens featuring colorful hydrangeas and tidy shrubbery. A private driveway is visible alongside the house, complemented by a rustic wooden fence that adds to the property's warmth. The front entrance is framed by seasonal blooms.