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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for South Dennis cottages

Exterior
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Cottage in Chatham

9.6 out of 10, Exceptional, (30)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
$277 nightly
The price is $317
Dec 14 - Dec 15
Total with taxes and fees
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Outdoor dining
🦀Waterfront at The Velvet Crab~Amazing Sunsets

Cottage in Eastham

9.8 out of 10, Exceptional, (23)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
$374 nightly
The price is $429
Jan 6 - Jan 7, 2026
Total with taxes and fees
🦀Waterfront at The Velvet Crab~Amazing Sunsets
Exterior
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

Cottage in Harwich

8.6 out of 10, Excellent, (4)
"Great accommodation for what we needed."
United States
Judith F.
$397 nightly
The price is $454
Dec 11 - Dec 12
Total with taxes and fees
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
Terrace/patio
Beautiful cottage, fireplace, cozy Beach 1. 4 mile . Family relaxation fire pit!

Cottage in Harwich

9.6 out of 10, Exceptional, (4)
"We had an amazing stay! The house was exactly what we were looking for when booking. The host was amazing and accommodating for our dates. Communication was easy and responsive. We look forward to booking again in the future. "
United States
Laura J.
$652 nightly
The price is $746
Dec 22 - Dec 23
Total with taxes and fees
Beautiful cottage, fireplace, cozy Beach 1. 4 mile . Family relaxation fire pit!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Dennis Hotel Reviews

Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"excellent quality of food. Pool and hot tub fabulous"
Deborah 2-night trip
Posted 1 day ago
Bayside Resort Hotel

Find out more about South Dennis

South Dennis Cottages information

Number of reviews
46
Accommodation
610 Cottages
Lowest Price
$317
Highest Price
$746

Frequently asked questions

How much do cottages in South Dennis cost?
Rates for cottages in South Dennis range between $317 and $746 per night. Whatever your budget, you'll find an ideal place to get reacquainted with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in South Dennis?
A traveler favorite is 16 Flakeyard Way - Four Bedroom House. Make yourself at home at this 3.5-star stay which comes with a water view and a patio. 10 Squanto Drive - One Bedroom House is another popular option worth a look. Unpack your suitcase at this 3.5-star cottage and you'll have access to amenities such as WiFi and clothes washing facilities. You'll have your pick of multiple cottages in South Dennis with a total average guest review rating of 9.4.
How many cottages are there in South Dennis?
Make use of your vacation days and choose from 610 cottages in South Dennis. Looking for a place where you can immerse yourself in nature? Expedia will help you find your ideal stay in only a click or two.
Are there any family-friendly cottages in South Dennis?
Many travelers needing a family-friendly cottage in South Dennis go for 16 Flakeyard Way - Four Bedroom House. With a 3.5-star rating and amenities such as WiFi and a patio, you're sure to feel at home here. Another great pick for families who crave a break close to nature is 10 Squanto Drive - One Bedroom House. WiFi and a fridge help make this 3.5-star cottage a great base for your South Dennis getaway. After checking in and chilling together in your cozy new digs, it's time to discover the local sights. Cape Cod Inflatable Park and Mayflower Beach are popular family-friendly attractions in South Dennis.
Why book your cottage in South Dennis with Expedia?
We think that a vacay should be hassle-free, so if you're looking for cottages in South Dennis at a nice price, Expedia has got you covered. Save cash and select a thrifty option far away from the hustle and bustle, or book an upmarket cottage to really spoil your favorite people.
How can I find cheap cottages in South Dennis?
A great way to uncover cheap cottages in South Dennis is with Expedia's handy filter tool. Refine your search by budget, amenities and star rating to nab unbeatable prices in just a few clicks.
What is there to do in South Dennis near my cottage?
Once you've unpacked your things and settled in, set out and explore the amazing things South Dennis has for you to experience. Cape Cod Rail Trail is a top attraction to add to your travel itinerary.

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