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

Tiny home in Wellfleet

4.98 out of 5 average rating, 226 reviews

Writer's Cabin in Woods near Wellfleet Bay

Our unique, creative and magical "Writer's Cabin" tiny house is a guest favorite! You'll be tucked in the woods with the views of a treehouse, and just minutes' drive or bike ride to Wellfleet's beaches, ponds & walking trails. Wellfleet's quaint town center and harbor are just a 10-15 minutes walk down the road. Note: the cabin has a private, wooden Nordic shower w/ hot water built onto the outside of the cabin. Our guests love this unique experience! The toilet is standard flushing & indoors.

Sep 23 – 28

G$37,632 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!!!

May 17 – 24

G$28,620 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 27 – Dec 4

G$37,104 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!

Feb 11 – 18

G$39,540 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

Dec 27 – Jan 3

G$36,285 GYD per night

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 149 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.

Feb 2 – 9

G$20,203 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.

Nov 23 – 30

G$35,968 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.

Oct 9 – 16

G$23,449 GYD per night

Guest favorite

Apartment in Barnstable

4.99 out of 5 average rating, 230 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!

Jan 30 – Feb 6

G$27,386 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.

May 3 – 10

G$27,365 GYD per night

Guest favorite

Condo in Dennis

4.84 out of 5 average rating, 164 reviews

The 5 minute walk to beach Super Cute Beach Condo

This conveniently located rental is just a 3 minute walk to the beach. This studio (245 sq ft) has 1 queen size bed, sleeper sofa, galley kitchen, dishes and silverware, pots and pans, refrigerator, microwave, coffee maker, WiFi, cable TV, beach chairs and umbrella and 2 boogie boards. There is a private patio with a table and a Webber Grill. PLEASE NOTE THE FOLLOWING: WE DO NOT PROVIDE LINENS OR TOWELS. THE BED IS QUEEN SIZE

Apr 23 – 30

G$15,811 GYD per night

Guest favorite

Apartment in Dennis

4.9 out of 5 average rating, 101 reviews

2 BD Suite Mayflower Beach & Dennis Village

This newly renovated, tastefully decorated 2nd floor suite is equipped with two bedrooms, one bathroom, living room and kitchen. During warmer months, a grill, fire-pit, ping pong table and bikes are available upon request. Located 1/4 mile off historic Rt 6A on Beach Street. Walking distance to Dennis Village Shops and top-rated restaurants. The house is 1 mile to beautiful Mayflower Beach.

Dec 22 – 29

G$38,558 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

Superhost

Cottage in Dennis

4.83 out of 5 average rating, 115 reviews

Adorable Cottage! Wlk 2 Beach! Cntrl AC! Fire Pit!

Jan 20 – 27

G$34,792 GYD per night

Guest favorite

Cottage in Dennis

4.94 out of 5 average rating, 102 reviews

Steps to the Beach Kid Friendly

May 7 – 14

G$60,136 GYD per night

Guest favorite

Guest suite in Hyannis

5.0 out of 5 average rating, 137 reviews

600 ft Walk to Ocean! Luxurious Renovated Cottage!

Apr 19 – 26

G$33,900 GYD per night

Superhost

Townhouse in Dennis

4.78 out of 5 average rating, 161 reviews

Windfall Townhouse - 1/2 mile to Nantucket Sound

May 13 – 20

G$33,823 GYD per night

Guest favorite

Guest suite in Orleans

4.92 out of 5 average rating, 142 reviews

Charming Old Cape Cod

Sep 24 – Oct 1

G$28,816 GYD per night

Guest favorite

Guest suite in Harwich

4.99 out of 5 average rating, 542 reviews

Romantic getaway suite

Feb 9 – 16

G$35,649 GYD per night

Guest favorite

Home in Dennis

4.94 out of 5 average rating, 269 reviews

Cape Cod Cottage by the Bay!

Jan 9 – 16

G$45,052 GYD per night

Guest favorite

Cottage in Dennis

4.95 out of 5 average rating, 191 reviews

The Strandloper / Beachwalker Cottage

Oct 4 – 11

G$42,440 GYD per night

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Dennis house rentals

Guest favorite

Home in Brewster

4.95 out of 5 average rating, 137 reviews

Brewster Home on Lower Mill Pond

Mar 19 – 26

G$34,792 GYD per night

Guest favorite

Home in Dennis

4.95 out of 5 average rating, 150 reviews

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

Nov 18 – 25

G$52,573 GYD per night

Guest favorite

Home in Dennis

4.98 out of 5 average rating, 247 reviews

Shirley's Place - Pet Friendly Sleeps Six!

Nov 1 – 8

G$38,513 GYD per night

Guest favorite

Home in Yarmouth Port, Cape Cod

4.99 out of 5 average rating, 311 reviews

Fabulous Waterfront! 3bdrm/2bth Kayaks & Firepit

Jan 14 – 21

G$167,983 GYD per night

Guest favorite

Home in Dennis

4.92 out of 5 average rating, 167 reviews

SUMMERS OFF CAPE HOUSE

Nov 30 – Dec 7

G$36,389 GYD per night

Superhost

Home in Dennis

4.87 out of 5 average rating, 459 reviews

Beachfront Cottage on White Pond (Marshmallow)

Sep 15 – 22

G$58,048 GYD per night

Superhost

Home in Dennis

4.79 out of 5 average rating, 138 reviews

Walk2Beach, HotTub, FirePit, PetsOk

Nov 7 – 14

G$73,214 GYD per night

Guest favorite

Home in Yarmouth Port

4.99 out of 5 average rating, 102 reviews

Historic Cape Retreat near Bike & Botanical Trail

Nov 13 – 20

G$60,227 GYD per night

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Beach house rentals in Dennis

Guest favorite

Home in Dennis

4.97 out of 5 average rating, 156 reviews

4 Minute Walk to Beach, Cape Cod Serenity

Oct 25 – Nov 1

G$48,154 GYD per night

Guest favorite

Home in Yarmouth

4.95 out of 5 average rating, 213 reviews

★Hot Tub★Pet OK★Firepit★Walk to Village&Beach★King

Dec 6 – 13

G$62,794 GYD per night

Guest favorite

Home in Yarmouth

4.91 out of 5 average rating, 117 reviews

Two Sisters’ Cape Escape (Sunroom,Large Deck, A/C)

Nov 16 – 23

G$37,287 GYD per night

Superhost

Home in Chatham

4.82 out of 5 average rating, 135 reviews

Delightful Chatham Cottage, Cheerful and Clean

May 27 – Jun 3

G$32,880 GYD per night

Superhost

Home in West Dennis

4.88 out of 5 average rating, 253 reviews

4BR/2BA SunSand&SeaHouse-Work remotely on Cape Cod

Mar 25 – Apr 1

G$70,137 GYD per night

Guest favorite

Home in Dennis

4.84 out of 5 average rating, 180 reviews

Walk to Beach! Cape Cod Comfy Home

Mar 22 – 29

G$85,471 GYD per night

Guest favorite

Home in Brewster

4.92 out of 5 average rating, 134 reviews

Cozy Cape Cabin - just minutes to Cape Cod Bay!

Nov 9 – 16

G$40,525 GYD per night

Guest favorite

Home in Chatham

4.96 out of 5 average rating, 191 reviews

Studio cottage in Chatham Ma.

Nov 12 – 19

G$35,880 GYD per night

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Quick stats about vacation rentals in Dennis

Total rentals
1.5K properties
Rentals with dedicated workspaces
480 properties have a dedicated workspace
Rentals with a pool
180 properties have a pool
Pet-friendly rentals
300 properties allow pets
Family-friendly rentals
1.2K properties are a good fit for families
Total number of reviews
39K reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Dennis?
Yes! Work meets play with ease at over 480 vacation rentals in Dennis featuring dedicated workspaces. Stay connected and productive 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 300 vacation rentals for guests traveling with pets.
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 Dennis vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 180 vacation homes 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 350 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 570 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 30 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 860 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Dennis vacation rentals

Top-rated vacation rentals in Dennis

Vacation rentals for every style

Houses

Apartments

Cottages

Popular amenities for Dennis vacation rentals

Stay near Dennis's top sights

Other great vacation rentals in Dennis

Cottage in Dennis

Cottage in Dennis

Guest suite in Hyannis

Townhouse in Dennis

Guest suite in Orleans

Guest suite in Harwich

Home in Dennis

Cottage in Dennis

Dennis house rentals

Home in Brewster

Home in Dennis

Home in Dennis

Home in Yarmouth Port, Cape Cod

Home in Dennis

Home in Dennis

Home in Dennis

Home in Yarmouth Port

Beach house rentals in Dennis

Home in Dennis

Home in Yarmouth

Home in Yarmouth

Home in Chatham

Home in West Dennis

Home in Dennis

Home in Brewster

Home in Chatham

Quick stats about vacation rentals in Dennis

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Dennis?

Are there pet-friendly vacation rentals in Dennis?

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

Are there Dennis vacation rentals on Airbnb with pools?

Do house rentals in Dennis have self check-in?

Do house rentals in Dennis have a bbq area?

Do house rentals in Dennis have a gym?

Are there family-friendly house rentals in Dennis?

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