Holiday rentals in Dennis

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Top-rated holiday rentals in Dennis

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A bright kitchen area is visible, featuring white cabinetry and modern appliances. A small dining table with two wooden stools is positioned near a window. The space is enhanced by natural light and wooden flooring, creating a welcoming atmosphere that connects to an adjoining living space.
Cottage in Dennis Port
4.89 out of 5 average rating, 105 reviews

Oyster Isle-Steps from the Beach!

A perfect seasonal escape, come enjoy the ocean waves and sunshine at this beach retreat! Spend time with family and friends exploring all the Cape has to offer in lively Dennis Port. Located steps from Haigas Beach, nearby playgrounds, ice cream shops, restaurants (Ocean House, Sandbar, Pelham House) and more. This 1 bedroom cottage comes fully equipped with a queen bed, beach essentials, outdoor shower, full kitchen & living space, A/C, parking, just steps from the beautiful Nantucket sound.

Top guest favourite
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
4.96 out of 5 average rating, 139 reviews

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

Top guest favourite
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
4.96 out of 5 average rating, 194 reviews

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!

Top guest favourite
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.
Cottage in Dennis Port
4.93 out of 5 average rating, 276 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

Top guest favourite
A charming cottage is surrounded by lush green trees and shrubs, set within a spacious yard. A gravel pathway leads to the entrance, while a wooden fence provides privacy. Flower boxes add a touch of color to the exterior near the windows.
Tiny home in South Yarmouth
4.89 out of 5 average rating, 635 reviews

Romantic Cottage w/ Bikes, Paddle Boards & Kayaks

This newly remodeled, nautically themed cottage includes countless amenities designed for a fun, romantic getaway with all the comforts of home. - Bikes, paddle boards, 2-person kayak, yard games, beach chairs/towels & cooler - Outdoor fire pit and gas grill - Stocked kitchen with quality cookware, organic coffee/tea, water filtration pitcher + more - Organic, vegan, unscented, allergen-free soaps & cleaning products - Extreme COVID sanitation protocols as well as quarterly deep cleanings

Top guest favourite
The light-filled living room features a spacious leather tufted couch positioned around a central ottoman. A flat-screen television is mounted on the wall above a cozy brick fireplace. Large windows allow natural light to brighten the room, with a glimpse of greenery visible outside.
Home in Yarmouth Port
4.99 out of 5 average rating, 132 reviews

Historic Cape Retreat near Bike & Botanical Trail

Enjoy this recently renovated historic home tastefully decorated in true Cape Cod fashion. This charming home is conveniently located just 0.6 miles to the bike trail, 1 mile to walking trails and 3 miles to Gray's Beach! Inside, you are greeted with a light filled living room. Walk upstairs to two bedrooms and a full bathroom. Enjoy the open kitchen that flows right into the dining room! Relax in the master bedroom and bathroom which is located on the other side of the house for privacy.

Top guest favourite
The exterior of a charming cottage is visible, featuring natural cedar shingles and a welcoming porch. Lush flower beds, including vibrant blue hydrangeas, frame the entrance, while a white picket fence adds to the quaint appeal. A well-maintained lawn enhances the home's inviting presence.
Home in Brewster
4.92 out of 5 average rating, 106 reviews

Antique Cape Home With Modern Conveniences

The Elisha Howland Saltbox provides your opportunity to experience the unmatched essence of a true 'Olde Cape Cod' home. We offer a restored antique Saltbox with 2 bedrooms and 2 bathrooms. For an additional charge, there is a detached cottage which can accommodate two more guests. PLEASE NOTE: we accept ONLY FULL WEEK RENTALS from mid-June to mid-September, but we welcome shorter or much longer stays during the rest of the year. Our home is a lovely place to spend a winter on Cape Cod.

Top guest favourite
A spacious backyard features a well-maintained lawn, surrounded by lush greenery. A wooden deck with seating overlooks the area, complemented by colorful flower pots. A hammock is nestled between trees, inviting relaxation. Comfortable chairs are arranged for outdoor enjoyment.
Guest suite in Harwich
4.99 out of 5 average rating, 632 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

Top guest favourite
The cottage showcases a classic Cape Cod design, framed by greenery and a gravel pathway. A standalone structure is visible with a sloped roof and a front door lined with dark shutters. Sunlight casts a warm glow on the exterior against a clear blue sky.
Home in East Dennis
4.93 out of 5 average rating, 318 reviews

Cape Cod Cottage by the Bay!

Classic, beautifully crafted, newer cottage by Cape Cod Bay. All amenities. Stainless steel kitchen, Cathedral ceilings, Wide plank wood floors, water view. 2 min walk to one of the best beaches on the Cape! Quiet locale in the historic village of Quivet Neck, within East Dennis. 35 miles to Provincetown. I do not allow pets. I have family members with severe allergies who use the cottage. There is no AC at this cottage. I have 15 windows, 4 fans and an ocean breeze.

Top guest favourite
A cozy studio space showcases a grey sofa with decorative cushions, positioned beside a small table featuring a fan. The kitchenette is visible in the background, equipped with white cabinetry and essential appliances. Natural light filters through a window, illuminating the warm and welcoming interior.
Flat in West Dennis
4.99 out of 5 average rating, 130 reviews

The Cape Cod Perch at West Dennis Beach Studio Apt

Take it easy at this unique and tranquil getaway just a short walk from three Nantucket Sound beaches. This 300-square-foot studio apartment on the second floor of our home. With a brand new Weber grill, picnic table, and fire pit, there is plenty of outside living. Trotting Park, South Village, and West Dennis Beaches are all walkable. Enjoy food from Sandbar, Swan River Seafood, Chapin's, Cleat & Anchor, & Bandera's Market in the summer. Call off season.

Guest favourite
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
4.86 out of 5 average rating, 564 reviews

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

Top guest favourite
A spacious suite features a cozy sleeping area with a queen bed dressed in soft linens. Natural light pours in through skylights above, illuminating the living area with a comfortable sofa and kitchenette. Wood beams add character to the high ceiling, creating a welcoming atmosphere.
Guest suite in South Yarmouth
4.99 out of 5 average rating, 266 reviews

Find Serenity in South Yarmouth - The Boat House

Welcome to The Boat House! Find a peaceful setting in this private suite nestled amid the charm of our one acre property. This nautical themed retreat provides a spacious yet cozy suite with private and exclusive entrance, and is outfitted with a queen bed, living and dining area, well-equipped kitchenette and full bath. The gas stove adds cozy ambiance for a night in while guests can also enjoy the beautiful backyard and koi pond.

Popular amenities for Dennis holiday rentals

When is the best time to visit Dennis?

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Frequently Asked Questions

  • Where should I stay in Dennis?

    Make yourself at home in Dennis by choosing from our most frequently booked neighborhoods. We have over 2,070 vacation rentals in Dennis Port, over 1,200 vacation rentals in Yarmouth Port, and over 2,070 vacation rentals in West Dennis.

  • What types of vacation rentals are available in Dennis?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Dennis. From over 200 cottage rentals to over 1,040 house rentals, we've got you covered.

  • Are there vacation rentals with a dedicated workspace in Dennis?

    Yes! Work meets play with ease at over 560 vacation rentals in Dennis featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in tiny house rentals in Dennis?

    Experience the best of Dennis with our tiny house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Dennis?

    Four-legged friends are welcome in Dennis. Choose from more than 370 vacation rentals for guests traveling with pets.

  • Are there Dennis house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 house rentals with pools in Dennis, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Dennis have self check-in?

    Absolutely! We offer over 300 house rentals with self check-in in Dennis. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Dennis have a bbq area?

    Absolutely! We offer over 470 house rentals with a bbq area in Dennis. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Dennis have a gym?

    Absolutely! We offer over 40 house rentals with a gym in Dennis. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Dennis?

    Dennis has more than 1,000 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Dennis

  • Total holiday rentals

    Explore 1,660 holiday rentals in Dennis

  • Nightly prices starting at

    Dennis holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 51,650 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,290 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 370 rentals that welcome pets

  • Holiday rentals with a pool

    230 properties feature pools

  • Rentals with dedicated workspaces

    560 properties have a dedicated workspace

  • Wifi availability

    1,640 of Dennis holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront and Gym across Dennis rentals

  • 4.8 Average rating

    Dennis stays are highly rated by guests – averaging 4.8 out of 5!

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