Orleans, MA Cottage Rentals from $355

Q: Are there any family-friendly cottages in Orleans?

Put your feet up at Cottages At The Even'tide Resort , a 2.5-star cottage just a quick drive from town. Amenities here include a playground and a picnic area. Another family-friendly pick where you can swap the urban jungle for open spaces is 16 Flakeyard Way - Four Bedroom House . WiFi and a patio help make this 3.5-star cottage a traveler favorite. After checking in and chilling out together in your comfy new digs, it's time to head out and explore the sights. Nauset Beach and Skaket Beach are top family-friendly attractions in Orleans.

Wooden beach chairs and a wooden staircase on a sandy beach with a hilly background.

Bundle & Save
Get more, spend less whenever you see Bundle & Save deals
OneKeyCash
Earn OneKeyCash on all your eligible bookings
Upfront pricing
We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Orleans cottages

1. On Town Cove with salt water access! Kayaks and paddle board available for use!

Eastham

Peter G.

$352 nightly

Sep 12 - Sep 13

Total with taxes and fees

2. 6 Mi to Beach: Home w/ Deck in Brewster!

Brewster

$603 nightly

Aug 17 - Aug 18

Total with taxes and fees

3. 🐳 The Whale Song - Dog-Friendly Studio

Eastham

Gregg P.

$310 nightly

Aug 23 - Aug 24

Total with taxes and fees

4. Eastham, Cape Cod - Town Cove Waterfront. Newly renovated and insulated sunporch

Eastham

Kathy D.

$514 nightly

Sep 1 - Sep 2

Total with taxes and fees

5. Castaway Cottage on the bay~Dog Friendly Too!

Eastham

Patty M.

6. The Breeze on Minister's Pond

Eastham

MelanieC

$599 nightly

Sep 4 - Sep 5

Total with taxes and fees

7. The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach

Wellfleet

$623 nightly

Sep 3 - Sep 4

Total with taxes and fees

8. Walk to Ocean Beach, Nat`l Seashore, WiFi, Bike Rail Trail

South Wellfleet

Donald W.

$656 nightly

Aug 16 - Aug 17

Total with taxes and fees

9. Beautiful cottage, Close to Wychmere & Beach, Family relax, king bed & fire pit!

Harwich

Laura J.

$706 nightly

Sep 2 - Sep 3

Total with taxes and fees

10. Private Cape Cod Cottage. Walk to Ellis Landing Beach!

Brewster

Samantha K.

$1,240 nightly

Aug 21 - Aug 22

Total with taxes and fees

11. Charming 18th century cottage with its own beachfront on Scargo Lake near bay

Dennis

Bruno M.

$697 nightly

Aug 20 - Aug 21

Total with taxes and fees

12. Harwich Hideaway with King Beds Pet Friendly!

Harwich

Colleen O.

$766 nightly

Aug 20 - Aug 21

Total with taxes and fees

13. Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

Harwich

Mia A.

$560 nightly

Sep 8 - Sep 9

Total with taxes and fees

14. 1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Hyannis

"The cottage is in a great location close to Main Street and the harbor. Easy parking at the cottage and it’s in a walkable area. Decor is cute and nautical, but it does feel like the cottage is missing a few things. It sleeps 4, but there is not enough seating for 4 in the living room. An additional comfortable chair would be nice. A stackable washer and dryer would also be great, but there is very little space for anything- we even had trouble finding spots for our luggage. The fridge door...

Christa

Beach nearby, sun loungers, beach towels

15. Mermaid Cottage! beautiful propety!

Dennis

Randy B.

$428 nightly

Aug 30 - Aug 31

Total with taxes and fees

16. Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

Barnstable

Helene M.

$470 nightly

Aug 19 - Aug 20

Total with taxes and fees

17. Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun

Yarmouth

Nicholas

$472 nightly

Aug 16 - Aug 17

Total with taxes and fees

18. The Perfect Shore Escape: The Sandpiper

Bass River

Michael C.

$448 nightly

Sep 8 - Sep 9

Total with taxes and fees

19. 5-Min Walk to Beach, 2 Cottages, Fire Pit, Pet Friendly

Dennis

$1,213 nightly

Sep 8 - Sep 9

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Private vacation homes

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Top Orleans Hotel Reviews

Margaritaville Resort Cape Cod

10/10 Excellent

"Beautifully renovated resort. We loved that the room keys were wrist bracelets, easy to keep track of. The room was clean, fun, nautical theme touches, and very comfortable bed. The pool and waterpark were super fun for kids, they also had a great arcade. We ate dinner at their restaurant Landshark, solid food, but the wait was extremely long. They did compensate us well with a free drink and dessert, which was much appreciated. The breakfast buffet was extra, but not too much, and also very good. The grounds had additional games such as cornhole, tetherball, and large chess. Music in the late afternoon in the courtyard was a nice touch. Highly recommend, will definitely be back!"

The Mariner Resort Cape Cod by The Red Collection

8/10 Good

"Hotel a great stay excellent location for what I was doing. Literally across the st from the inflatable park. Also has miniature golf on site 2 pools a play ground and free breakfast. Although breakfast could be better my kids enjoyed making there waffles. Only complaint is I requested a late check out for 12 and which was approved... I was resting my last 20 mins before my long trip home and house keeping decides to knock on the door and walk in. I explained I have late check out until 12. She argued with me that it was only until 11:30, kept talking over me then basically called me a liar and slammed the door closed. I informed the front desk about the issue they did nothing but apologize and confirm that my check out was in fact at 12. Customer service can certainly be improved"

Red Jacket Beach Resort

10/10 Excellent

"The hotel is great and we had a wonderful time! My 2 kids had so much fun playing all the sports they offer and swimming at the beach. The beach is beautiful and rooms are clean and the staff very friendly and helpful! The only negative point is being charged $25 per night for the parking lot."

Find out more about Orleans

Orleans Cottages information

Number of reviews	365
Accommodation	530 Cottages
Lowest Price	$355
Highest Price	$1,419

Frequently asked questions

How much do cottages in Orleans cost?

Rates for cottages in Orleans range between $355 and $1,419 per night. Whatever your budget, you'll find the ideal place to reconnect 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 Orleans?

Orleans has multiple cottages with a total average guest review rating of 9.4. Cottages At The Even'tide Resort is a terrific option if you're into nature and an easy-breezy pace. Visitors staying at this 2.5-star stay can enjoy amenities such as a terrace and a swimming pool. 16 Flakeyard Way - Four Bedroom House is another popular pick. This 3.5-star cottage features a water view and a patio.

How many cottages are there in Orleans?

You'll find 530 cottages in Orleans. No matter if you're vacationing with the family or organizing a weekend retreat with your closest amigos, Expedia will help you find the ideal property to get in touch with nature.

Are there any family-friendly cottages in Orleans?

Put your feet up at Cottages At The Even'tide Resort, a 2.5-star cottage just a quick drive from town. Amenities here include a playground and a picnic area. Another family-friendly pick where you can swap the urban jungle for open spaces is 16 Flakeyard Way - Four Bedroom House. WiFi and a patio help make this 3.5-star cottage a traveler favorite. After checking in and chilling out together in your comfy new digs, it's time to head out and explore the sights. Nauset Beach and Skaket Beach are top family-friendly attractions in Orleans.

Why book your cottage in Orleans with Expedia?

We think that traveling should be easy, so if you're looking for cottages in Orleans at a competitive rate, Expedia has you covered. Save cash and stay in a thrifty option far from the rush of the city, or splurge on a 5-star cottage to pamper your favorite people.

How can I find cheap cottages in Orleans?

With Expedia's user-friendly filter tool, comparing cheap cottages in Orleans couldn't be simpler. To discover properties that'll make your bank balance smile, fine-tune your search results by amenities, budget and star rating.

What is there to do in Orleans near my cottage?

Whatever you love doing, Orleans has plenty to keep you on the move. Cape Escape Adventure Golf, Academy Playhouse and Orleans Historical Society Meeting House Museum are on many travelers' sightseeing itineraries. You shouldn't miss Jonathan Young Windmill, Addison Art Gallery and Skaket Beach either. With Expedia's Orleans hotel deals, you'll be able to discover even more neat attractions like these with the cash you save.

Room 1

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Orleans cottages

1. On Town Cove with salt water access! Kayaks and paddle board available for use!

2. 6 Mi to Beach: Home w/ Deck in Brewster!

3. 🐳 The Whale Song - Dog-Friendly Studio

4. Eastham, Cape Cod - Town Cove Waterfront. Newly renovated and insulated sunporch