Dennis vacation rentals

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Top-rated vacation rentals in Dennis

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

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Guest favorite

Place to stay in Wellfleet

4.98 out of 5 average rating, 163 reviews

WoodsideTiny House near Wellfleet Bay

Our tiny house tucked under trees is the perfect getaway. Walk past our orchard to get to your "Romantic Hideaway". This special rental has a private, sunny deck, a Nordic shower, stained glass windows and a library of books/vinyls. Set back from a quiet road on our property, this little gem is walking distance to Wellfleet's center, harbor & many restaurants, & just minutes drive from National Seashore beaches & ponds. A fun time in bustling Provincetown awaits you only 15 miles down the road!

Sep 19 – 26

G$35,325 GYD per night

Guest favorite

Condo in Dennis

4.99 out of 5 average rating, 172 reviews

Studio, 300 yards to Glendon Beach; Seahorse#2

Newly renovated, 250 sq ft studio at Near Beach Rentals. 300 yards to Glendon Beach means you can head to the beach in the morning and you're close enough to walk back for lunch. Fully furnished studio includes a queen bed and a fold down couch, kitchen with stove, fridge, coffee maker and microwave, air conditioning, 40" smart TV, newly renovated bathroom, Wifi, and access to the shared courtyard with grills and furniture. **(6) total units makes NBR a great place for larger gatherings!!!

Oct 12 – 19

G$26,185 GYD per night

Guest favorite

Cottage in Dennis

4.94 out of 5 average rating, 216 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

Nov 30 – Dec 7

G$36,319 GYD per night

Guest favorite

Guest suite in Yarmouth

4.99 out of 5 average rating, 245 reviews

Sweet Little Suite in South Yarmouth

Welcome to the Jelly Shop! Enjoy your own free-standing, private cottage on this beautiful family-owned compound. This cozy retreat will provide ample living space, romantic captain's bed, kitchenette with fridge, microwave and Keurig coffeemaker. Enjoy your own private patio for lounging and dining. A beautiful stroll through this historic neighborhood will bring you to the Windmill on Bass River and close enough to other beaches, year-round attractions, restaurants and more! Welcome!

Dec 30 – Jan 6

G$39,396 GYD per night

Guest favorite

Tiny home in S. Yarmouth

4.88 out of 5 average rating, 538 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

Oct 31 – Nov 7

G$36,215 GYD per night

Guest favorite

Apartment in Falmouth

4.98 out of 5 average rating, 115 reviews

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

Oct 25 – Nov 1

G$14,621 GYD per night

Guest favorite

Guest suite in Harwich

4.99 out of 5 average rating, 543 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Nine 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.

Nov 26 – Dec 3

G$31,968 GYD per night

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 150 reviews

Cozy and Secluded Apartment/Seasonal garden view

Walk across your private patio through sliding glass doors to your private garden retreat in this spacious studio. A large bathroom is just off the kitchen. This brand new apartment is designed for your perfect vacation or retreat from city life. If you are working from home - try working from Cape Cod! A desk awaits you - leave your computer set up and ready! Not the best apartment for disabilities - the entrance is in the back and there is a step up into the shower.

Dec 14 – 21

G$19,858 GYD per night

Guest favorite

Cottage in Bourne

5.0 out of 5 average rating, 143 reviews

140 Steps to Beach with Water Views

This small rustic unique cottage is ready for you to enjoy on Buttermilk Bay. It is located within a cape style cottage community that offers a private association beach. There are water views from both the living room and deck. Grab the provided beach chairs, water tubes, cooler and walk a 140 steps from the deck to the beach. You can also Walk or Bike on Cape Cod Canal, 5 min. Close to restaurants, hiking trails and Cape Cod Bridge -5 min away. 20% off wk.

Apr 13 – 20

G$28,271 GYD per night

Guest favorite

Guesthouse in Yarmouth

4.96 out of 5 average rating, 183 reviews

One bedroom guest house on beautiful Cape Cod

Second level guest apartment with one bedroom, bathroom, kitchen, large walk-in closet and living room. Just about everything you need to feel at home. There is A/C in the bedroom and the living area is well vented and has a large ceiling fan. Two golf courses are within 3/4 of a mile, public access beach and boat ramp are within 1 mile. You will also find kayaking, bike trails, walking trails and many other Cape Cod amenities just a short drive away.

Mar 18 – 25

G$35,898 GYD per night

Guest favorite

Apartment in Barnstable

4.99 out of 5 average rating, 231 reviews

Your dog will love it here and you will too.

If you love to travel with your dog (dogs), like I do, then this is the perfect place for you and your dog. We have a large fenced in yard for your dog to play in and for you to relax in with your dog. We have a one bedroom apartment with a full kitchen, bath, living room and dining area When you book would you PLEASE let me know whether or not you will be traveling with a dog and if you are what breed of dog will you be bringing. Thanks!

Feb 19 – 26

G$27,333 GYD per night

Guest favorite

Guest suite in Harwich

4.94 out of 5 average rating, 226 reviews

Cape Hideaway

Private suite on the first floor guests have exclusive use of the entire place. The second floor is my residence. The suite has a bedroom with queen temperpedic mattress, living room with queen sleep sofa, small kitchenette and bath. The kitchen is equipped with a small refrigerator, microwave, coffee maker, kettle, single burner cooktop and crockpot. Guests have access to the upper deck (shared space) which has a patio set and gas grill.

Nov 26 – Dec 3

G$27,312 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Dennis vacation rentals

Laptop-friendly workspace

Stay near Dennis's top sights

West Dennis Beach83 locals recommend

Captain Parker's Pub81 locals recommend

Sesuit Harbor Cafe167 locals recommend

Kream 'n Kone58 locals recommend

Pirate's Cove Adventure Golf130 locals recommend

Whydah Pirate Museum111 locals recommend

Other great vacation rentals in Dennis

Guest favorite

Home in Dennis

4.94 out of 5 average rating, 270 reviews

Cape Cod Cottage by the Bay!

Dec 13 – 20

G$47,004 GYD per night

Guest favorite

Cottage in Dennis Port

4.95 out of 5 average rating, 191 reviews

The Strandloper / Beachwalker Cottage

Dec 16 – 23

G$42,052 GYD per night

Guest favorite

Guest suite in Wellfleet

4.95 out of 5 average rating, 170 reviews

Wellfleet Get Away

Oct 5 – 12

G$33,838 GYD per night

Guest favorite

Guest suite in Yarmouth

4.85 out of 5 average rating, 249 reviews

Old Cape Cottage

Sep 24 – Oct 1

G$33,309 GYD per night

Guest favorite