Title: Chatham Vacation Rentals from $138: Search Short-Term Rentals | Expedia.com

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![Chatham showing a windmill, wildflowers and general coastal views](https://images.trvl-media.com/place/10743/d3f8b886-55a4-46b3-afab-39fd14b1b518.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/10743/d3f8b886-55a4-46b3-afab-39fd14b1b518.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=10743&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=10743&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=10743&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=10743&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chatham vacation rentals

![TV, fireplace, books](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/7e1e24c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/49d1d00f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/e4387afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/203d6415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

[](https://www.expedia.com/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.Hotel-Information)

Chatham

9.6/10

Exceptional

(102 reviews)

"Our second year in a row staying here. Cute house and great location! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Erin M.

$415 nightly

$475 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/126000000/125260000/125255600/125255521/w1799h1199x1y1-55128dae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/126000000/125260000/125255600/125255521/w1799h1199x1y1-1b750c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125260000/125255600/125255521/w1799h1199x1y1-bb36cf90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/126000000/125260000/125255600/125255521/w1799h1199x1y1-879fd999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Chatham Retreat. Walk to Main St & Beach

[](https://www.expedia.com/Chatham-Hotels-Luxury-Chatham-Retreat-Walk-To-Main-St-Beach.h125255521.Hotel-Information)

Chatham

$601 nightly

$688 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Chatham-Hotels-Luxury-Chatham-Retreat-Walk-To-Main-St-Beach.h125255521.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33710000/33705700/33705690/58cbf5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/34000000/33710000/33705700/33705690/3da525ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33705700/33705690/ff5b375b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/34000000/33710000/33705700/33705690/f6e7ab11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

[](https://www.expedia.com/Chatham-Hotels-Quaint-Cozy-Downtown-Chatham-Home.h33705690.Hotel-Information)

Chatham

10/10

Exceptional

(117 reviews)

"Clean, quiet, and great location."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tyler B.

$431 nightly

$493 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Chatham-Hotels-Quaint-Cozy-Downtown-Chatham-Home.h33705690.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/109000000/108280000/108276700/108276630/55ac4f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108280000/108276700/108276630/9dda4a64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/109000000/108280000/108276700/108276630/fa847e13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108280000/108276700/108276630/1b973fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

[](https://www.expedia.com/Brewster-Hotels-Coastal-Cape-Cod-3-Bedroom-Home-Close-To-The-Beach.h108276630.Hotel-Information)

West Brewster

10/10

Exceptional

(25 reviews)

"Lovely house with nice location."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

amy d.

$603 nightly

$690 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Brewster-Hotels-Coastal-Cape-Cod-3-Bedroom-Home-Close-To-The-Beach.h108276630.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105960000/105950400/105950370/333a1f76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/106000000/105960000/105950400/105950370/w1280h884x0y3-f8eab3b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105950400/105950370/c695a9a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105960000/105950400/105950370/1233c7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

[](https://www.expedia.com/Dennis-Port-Hotels-Cottage-Oasis-By-Lake-With-Kayaks.h105950370.Hotel-Information)

Dennis

8.8/10

Excellent

(3 reviews)

"Very cute cottage. Very clean and grounds well manicured. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveler

$281 nightly

$311 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Dennis-Port-Hotels-Cottage-Oasis-By-Lake-With-Kayaks.h105950370.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69630000/69627400/69627390/74737667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69630000/69627400/69627390/w1440h1072x0y4-774c8ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/70000000/69630000/69627400/69627390/43593282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/70000000/69630000/69627400/69627390/d6ef4bc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 🦀Waterfront at The Velvet Crab\~Amazing Sunsets

[](https://www.expedia.com/Eastham-Hotels-Waterfront-At-The-Velvet-CrabAmazing-Sunsets.h69627390.Hotel-Information)

Eastham

9.8/10

Exceptional

(23 reviews)

"Everything was great, we really enjoyed our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anna T.

$365 nightly

$418 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Eastham-Hotels-Waterfront-At-The-Velvet-CrabAmazing-Sunsets.h69627390.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113410000/113402100/113402058/5599a184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113410000/113402100/113402058/b2ffc4ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113410000/113402100/113402058/088bfd65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113410000/113402100/113402058/269acbc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

[](https://www.expedia.com/Eastham-Hotels-Solace-In-The-Sun-Adj-BedsGame-RoomSoakng-Tub.h113402058.Hotel-Information)

Eastham

10/10

Exceptional

(2 reviews)

"The house was beautiful, tucked away, and clean. It was spacious for two families with room for more comfortably. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

michele I.

$576 nightly

$659 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Eastham-Hotels-Solace-In-The-Sun-Adj-BedsGame-RoomSoakng-Tub.h113402058.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/c5192e69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, Netflix, books](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/c100b426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, Netflix, books](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/a58600d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/a7d1d86a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

[](https://www.expedia.com/Brewster-Hotels-Cheery-House-Wdeck.h72434954.Hotel-Information)

West Brewster

9.6/10

Exceptional

(50 reviews)

"House was perfect for our family reunion! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gregg H.

$516 nightly

$590 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Brewster-Hotels-Cheery-House-Wdeck.h72434954.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/73000000/72060000/72057400/72057337/67e7efb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72060000/72057400/72057337/6abdb82f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/73000000/72060000/72057400/72057337/4439aa97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/73000000/72060000/72057400/72057337/d0678136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleeps 2-8/Soaking Tub/FirePit\~Burrows

[](https://www.expedia.com/Eastham-Hotels-New-Listing-A-Perfect-Warm-Cozy-Cape-Getaway.h72057337.Hotel-Information)

Eastham

10/10

Exceptional

(7 reviews)

"Overall, we had a really great stay. The home is in a quiet neighborhood & close to the beach. Everything was clean and as described in the listing. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kallee M.

$437 nightly

$501 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Eastham-Hotels-New-Listing-A-Perfect-Warm-Cozy-Cape-Getaway.h72057337.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/104000000/103810000/103804400/103804342/1e6789c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103810000/103804400/103804342/8abef419.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103810000/103804400/103804342/0f4547ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103810000/103804400/103804342/ceca8394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Large Home in Harwich with Patio near Wequassett Resort

[](https://www.expedia.com/Harwich-Hotels-Cozy-Large-Home-In-Harwich-With-Patio-Near-Wequassett-Resort.h103804342.Hotel-Information)

Harwich

9.8/10

Exceptional

(11 reviews)

"Host was very responsive and the house provided everything we needed. Great location! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ashley M.

$459 nightly

$508 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Harwich-Hotels-Cozy-Large-Home-In-Harwich-With-Patio-Near-Wequassett-Resort.h103804342.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/107000000/106620000/106616600/106616596/3a8b4a5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106620000/106616600/106616596/ab42d5ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106620000/106616600/106616596/ecb64c40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106620000/106616600/106616596/68daf8e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coastal Haven in West Dennis

[](https://www.expedia.com/West-Dennis-Hotels-Coastal-Haven-In-West-Dennis.h106616596.Hotel-Information)

Dennis

10/10

Exceptional

(3 reviews)

"Overall the property was perfect. Great location, super clean and plenty of room for our family of 4\. The only negative I can say is that the property is a duplex and that’s not mentioned in the listing. Overall great spot and would stay there again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Edward R.

$543 nightly

$588 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/West-Dennis-Hotels-Coastal-Haven-In-West-Dennis.h106616596.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/42000000/41190000/41180500/41180439/788d515a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/42000000/41190000/41180500/41180439/ac9e3c9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/42000000/41190000/41180500/41180439/14f7698a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/42000000/41190000/41180500/41180439/b1d295be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

[](https://www.expedia.com/Eastham-Hotels-King-BedHot-TubWaterfront-The-Lotus.h41180439.Hotel-Information)

Eastham

10/10

Exceptional

(19 reviews)

"Just a great location, and a very comfortable place. We loved the porch bed and chair. We are looking forward to returning."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

David B.

$428 nightly

$490 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Eastham-Hotels-King-BedHot-TubWaterfront-The-Lotus.h41180439.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/ec7f5979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/3bdd02f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/40c1b64d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/6d5b6832.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Beach & Pond Getaway; Heart of Cape Cod

[](https://www.expedia.com/South-Yarmouth-Hotels-Homey-Central-Vacay-W-Game-Room-Near-Beach-And-Pond.h76664195.Hotel-Information)

South Yarmouth

10/10

Exceptional

(12 reviews)

"Great location and very comfortable rental home. Everything you need is included and the house is well stocked and clean!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dennis S.

$487 nightly

$557 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/South-Yarmouth-Hotels-Homey-Central-Vacay-W-Game-Room-Near-Beach-And-Pond.h76664195.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/35000000/34020000/34010200/34010162/a2f5ff90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34020000/34010200/34010162/270-a367fa95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34020000/34010200/34010162/c4d26f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34020000/34010200/34010162/d3048208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family Cottage Close to Beach!!

[](https://www.expedia.com/Harwich-Port-Hotels-Family-Cottage-Close-To-Beach.h34010162.Hotel-Information)

Harwichport

9.8/10

Exceptional

(75 reviews)

"Everything was exactly as described - they provided beach towels and chairs which we used - the property was perfect for our stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John N.

$714 nightly

$817 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Harwich-Port-Hotels-Family-Cottage-Close-To-Beach.h34010162.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/96000000/95140000/95132700/95132664/d6513126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95140000/95132700/95132664/d961202a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/96000000/95140000/95132700/95132664/dda22c4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/96000000/95140000/95132700/95132664/46a3fe6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

[](https://www.expedia.com/Brewster-Hotels-Ocean-Edge-Cape-Cod-2-Bed-2-Bath.h95132664.Hotel-Information)

Brewster

10/10

Exceptional

(42 reviews)

"Great place!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael P.

$319 nightly

$365 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Brewster-Hotels-Ocean-Edge-Cape-Cod-2-Bed-2-Bath.h95132664.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/abe7cc3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/2d001dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/01e797f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/180-2a992e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

[](https://www.expedia.com/South-Wellfleet-Hotels-Spectacular-Private-Waterfront-Cottage-On-Bayside-Panoramic-Views-Pet-Friendly.h22960042.Hotel-Information)

Wellfleet

10/10

Exceptional

(79 reviews)

"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Janice H.

$391 nightly

$448 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/South-Wellfleet-Hotels-Spectacular-Private-Waterfront-Cottage-On-Bayside-Panoramic-Views-Pet-Friendly.h22960042.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/90000000/89770000/89767900/89767890/f2144f62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/90000000/89770000/89767900/89767890/933367ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89770000/89767900/89767890/d4814c2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/90000000/89770000/89767900/89767890/7255c893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Pet-Friendly Surf Shack Hideaway on the Cove

[](https://www.expedia.com/Eastham-Hotels-The-Pet-Friendly-Surf-Shack-Hideaway-On-The-Cove.h89767890.Hotel-Information)

Eastham

10/10

Exceptional

(22 reviews)

"We loved the luxury bed linens, large kitchen & living area & the fact that it was pet friendly in a lovely neighborhood!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer G.

$430 nightly

$493 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Eastham-Hotels-The-Pet-Friendly-Surf-Shack-Hideaway-On-The-Cove.h89767890.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117600000/117596900/117596856/8ee96842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117600000/117596900/117596856/7682a80a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117600000/117596900/117596856/dd3082d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117600000/117596900/117596856/977262d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Driftmoor\~Dog Frndly 3bd/2 bth\~Luxe

[](https://www.expedia.com/Eastham-Hotels-DriftmoorDog-Frndly-3bd2-BthLuxe.h117596856.Hotel-Information)

Eastham

$470 nightly

$538 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Eastham-Hotels-DriftmoorDog-Frndly-3bd2-BthLuxe.h117596856.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/101000000/100820000/100813500/100813406/7ba4d94e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100820000/100813500/100813406/7409298e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100820000/100813500/100813406/7f0dab22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100820000/100813500/100813406/670dfc55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New! Island Pines-A Dog Friendly Boutique Oasis

[](https://www.expedia.com/Wellfleet-Hotels-New-Island-Pines-A-Dog-Friendly-Boutique-Oasis.h100813406.Hotel-Information)

Wellfleet

9.4/10

Exceptional

(11 reviews)

"Loved the place. Very clean and updated. You have to time the tides because it is on an island, but that was fine for us. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brian F.

$479 nightly

$549 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Wellfleet-Hotels-New-Island-Pines-A-Dog-Friendly-Boutique-Oasis.h100813406.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69400000/69397500/69397439/c0db5e1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/70000000/69400000/69397500/69397439/a7bbdf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/70000000/69400000/69397500/69397439/74272731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, travel crib, WiFi](https://images.trvl-media.com/lodging/70000000/69400000/69397500/69397439/598d00d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cape Cod Villa pond front vacation home, retreat, spa, venue, film location

[](https://www.expedia.com/Harwich-Hotels-Pond-Front-In-The-Woods.h69397439.Hotel-Information)

Harwich - Brewster Border

10/10

Exceptional

(6 reviews)

"Lovely property with attentive hosts "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

marian t.

$1,057 nightly

$1,210 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Harwich-Hotels-Pond-Front-In-The-Woods.h69397439.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-12&endDate=2026-03-13&regionId=10743&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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[Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_10743)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+Massachusetts%2C+United+States+of+America&regionId=10743&latLong=41.682602%2C-69.961624&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+Massachusetts%2C+United+States+of+America&regionId=10743&latLong=41.682602%2C-69.961624&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=COTTAGE)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+Massachusetts%2C+United+States+of+America&regionId=10743&latLong=41.682602%2C-69.961624&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=CONDO)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+Massachusetts%2C+United+States+of+America&regionId=10743&latLong=41.682602%2C-69.961624&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+Massachusetts%2C+United+States+of+America&regionId=10743&latLong=41.682602%2C-69.961624&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+Massachusetts%2C+United+States+of+America&regionId=10743&latLong=41.682602%2C-69.961624&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=VILLA)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+Massachusetts%2C+United+States+of+America&regionId=10743&latLong=41.682602%2C-69.961624&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=CABIN)

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## Top Chatham Hotel Reviews

![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg)

### Margaritaville Resort Cape Cod

10/10 Excellent

"Excellent ❤️❤️"

[](https://expedia.com/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information)

![Edgewater Beach Resort, a VRI resort](https://images.trvl-media.com/lodging/2000000/1530000/1522300/1522228/5e9e9f5c_y.jpg)

### Edgewater Beach Resort, a VRI resort

10/10 Excellent

"Clean rooms, excellent staff. "

[](https://expedia.com/Dennis-Port-Hotels-Edgewater-Beach-Resort.h1522228.Hotel-Information)

![Bayside Resort Hotel](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/85f07916_y.jpg)

### Bayside Resort Hotel

10/10 Excellent

"Clean and good size room, friendly staff, Expedia gold status perks, quiet on the 2nd floor, excellent complimentary breakfast"

[](https://expedia.com/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information)

![Courtyard Resort](https://images.trvl-media.com/lodging/116000000/115250000/115243800/115243739/5d7ebe6e_y.jpg)

### Courtyard Resort

10/10 Excellent

"Everything was good,location was spot on,we'll be back."

[](https://expedia.com/Hyannis-Hotels-Courtyard-Resort.h115243739.Hotel-Information)

![Aiden by Best Western Cape Cod - West Yarmouth](https://images.trvl-media.com/lodging/39000000/38360000/38357900/38357891/03e2a40a_y.jpg)

### Aiden by Best Western Cape Cod - West Yarmouth

10/10 Excellent

"Friendliness clean rooms Good breakfast clean pool"

[](https://expedia.com/West-Yarmouth-Hotels-Aiden-By-Best-Western-Cape-Point.h38357891.Hotel-Information)

![Chatham Wayside Inn](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002_y.jpg)

### Chatham Wayside Inn

10/10 Excellent

"Friendly staff, clean and spacious room, convenience of having a restaurant on site, and convenience of walking to all the stores and restaurants. "

[](https://expedia.com/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information)

![Hyannis Plaza Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1119300/1119277/f7fc1d07_y.jpg)

### Hyannis Plaza Hotel

10/10 Excellent

"Good"

[](https://expedia.com/Hyannis-Hotels-Hyannis-Plaza-Hotel.h1119277.Hotel-Information)

![Chatham Bars Inn](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg)

### Chatham Bars Inn

10/10 Excellent

"Beautiful property "

[](https://expedia.com/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information)

![The Mansion at Ocean Edge](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/5d8fbc52_y.jpg)

### The Mansion at Ocean Edge

10/10 Excellent

"Didnt overlook beach."

[](https://expedia.com/Brewster-Hotels-The-Mansion-At-Ocean-Edge.h7948.Hotel-Information)

## Find out more about Chatham

**Everything you need to know about Chatham vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chatham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chatham vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chatham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chatham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $138 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Chatham rentals**

At Expedia, we put the best Chatham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chatham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Chatham ](https://expedia.com/Chatham-Private-Vacation-Homes.d10743-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Chatham ](https://expedia.com/Chatham-Cottages.d10743-aaCottages.Travel-Guide-Accommodation)
- [Condo Rentals in Chatham ](https://expedia.com/Chatham-Condos.d10743-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Chatham ](https://expedia.com/Chatham-Apartments.d10743-aaApartments.Travel-Guide-Accommodation)
- [Motels in Chatham ](https://expedia.com/Chatham-Motels.d10743-aaMotels.Travel-Guide-Accommodation)
- [B&B in Chatham ](https://expedia.com/Chatham-Bed-And-Breakfast.d10743-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Chatham ](https://expedia.com/Chatham-Guest-Houses.d10743-aaGuestHouses.Travel-Guide-Accommodation)
- [Resorts in Chatham ](https://expedia.com/Chatham-Resorts.d10743-aaResorts.Travel-Guide-Accommodation)
- [Aparthotels in Chatham ](https://expedia.com/Chatham-Apart-Hotels.d10743-aaApartHotels.Travel-Guide-Accommodation)
- [Villas in Chatham ](https://expedia.com/Chatham-Villas.d10743-aaVillas.Travel-Guide-Accommodation)
- [Lodges in Chatham ](https://expedia.com/Chatham-Lodges.d10743-aaLodges.Travel-Guide-Accommodation)
- [Inns in Chatham ](https://expedia.com/Chatham-Inns.d10743-aaInns.Travel-Guide-Accommodation)
- [Cabin Rentals in Chatham ](https://expedia.com/Chatham-Cabins.d10743-aaCabins.Travel-Guide-Accommodation)
- [Hostels in Chatham ](https://expedia.com/Chatham-Hostels.d10743-aaHostels.Travel-Guide-Accommodation)
- [Condo Resorts in Chatham ](https://expedia.com/Chatham-Condominium-Resort.d10743-aaCondominiumResort.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Chatham?

### What are some of the best vacation rentals that Chatham has to offer?

### How many vacation rentals are there in Chatham?

### What can I see and do in Chatham?

### What are vacation rentals like in Chatham?

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- [Hotels in South Yarmouth](https://expedia.com/South-Yarmouth-Hotels.d7627.Travel-Guide-Hotels)
- [Hotels in Lowell](https://expedia.com/Lowell-Hotels.d8422.Travel-Guide-Hotels)
- [Hotels in Brockton](https://expedia.com/Brockton-Hotels.d7068.Travel-Guide-Hotels)
- [Hotels in Nantucket](https://expedia.com/Nantucket-Hotels.d285.Travel-Guide-Hotels)
- [Hotels in West Springfield](https://expedia.com/West-Springfield-Hotels.d7738.Travel-Guide-Hotels)
- [Hotels in Rockport](https://expedia.com/Rockport-Hotels.d6350.Travel-Guide-Hotels)
- [Hotels in Northampton](https://expedia.com/Northampton-Hotels.d9187.Travel-Guide-Hotels)
- [Hotels in Falmouth](https://expedia.com/Falmouth-Hotels.d7287.Travel-Guide-Hotels)
- [Hotels in Worcester](https://expedia.com/Worcester-Hotels.d6023336.Travel-Guide-Hotels)
- [Hotels in Marlborough](https://expedia.com/Marlborough-Hotels.d8869.Travel-Guide-Hotels)
- [Hotels in Lenox](https://expedia.com/Lenox-Hotels.d8587.Travel-Guide-Hotels)
- [Hotels in Gloucester](https://expedia.com/Gloucester-Hotels.d8008.Travel-Guide-Hotels)
- [Hotels in New Bedford](https://expedia.com/New-Bedford-Hotels.d1180.Travel-Guide-Hotels)

Cars

- [Car rentals in Mansfield](https://expedia.com/Car-Rentals-In-Mansfield.d8456.Car-Rental-Guide)
- [Car rentals in Springfield](https://expedia.com/Car-Rentals-In-Springfield.d6047669.Car-Rental-Guide)
- [Car rentals in Worcester](https://expedia.com/Car-Rentals-In-Worcester.d6023336.Car-Rental-Guide)

Activities

- [Things to do in Hyannis](https://expedia.com/Things-To-Do-In-Hyannis.d1544.Travel-Guide-Activities)

Packages

- [Nantucket Vacation](https://expedia.com/Nantucket.d285.Destination-Travel-Guides)

Vacation Rentals

- [Nantucket Vacation Rentals](https://expedia.com/Nantucket-Vacation-Rentals.d285.Travel-Guide-VacationRentals)

General

- [Visit Manchester-by-the-Sea](https://expedia.com/Manchester-By-The-Sea.dx129363)
- [Visit Rockport](https://expedia.com/Rockport.dx6350)

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