Vacation Rentals for Early Bookings

Want to get a jump on your summer plans for next summer? See what's already taking bookings here. 

Vacation Rental -- Dog friendly with access to Bass River

83 Bay Ridge Drive South Dennis MA 02660
For Rent

Listing Number 83bayridge

  • Exclusive Vacation Rentals
  • Village South Dennis
  • Bathroom 2
  • Maximum Occupants 7
  • Bedrooms 3

  Welcome to Dennis! Sit back and relax in this 3 bedroom, 2 bath, dog friendly home with private access to Bass River just 1,500 feet away and 0.5 mile to Flax Pond Conservation Area with one of the few dog friendly beaches in the area.  The home sleeps 7 and comes with a Smart TV, A/C (wall splits and window units) and linens provided. The main bedroom has two mini split A/Cs, ceiling fan, king bed, and quiet sitting areas to enjoy a book or your morning coffee. The second bedroom has double bed and window A/C. The third bedroom has two twin beds and window A/C. Need just a little more space? The downstairs bonus room couch pulls out into a twin bed and has a split A/C.  And since you are bringing Fido, the basement has a washer and dryer and we provide sheets and towels. But don't spend all your time inside in the A/C, enjoy the patio and sit under the umbrella at the patio table. Going for a swim? Rinse off in the outdoor shower and then turn on the gas grill to cook that 29" striper you are about to tell all your friends was 48".     Ready to get out and explore the area?  Flax Pond Conservation Area in Dennis has miles of trails and a dog friendly beach to cool off.  Across Mayfair Road you can access Bass River with canoes, kayaks, and SUPs to explore the area by water.  You are also centrally located in Dennis so getting to the Northside and Southside beaches is equally easy and allows for easy access to shopping and the highway in case you want to venture farther down Cape.  Are you a biking enthusiast? Hop on the nearby Cape Cod Rail Trail junction on Route 134 giving you access to the entire bike trail running from Wellfleet to the newly finished sections in Yarmouth. This home is also available for off season getaways and is fully heated for a winter retreat.  For up to date pricing and availability click here Amenities: Dog friendly Washer/dryer and linens provided A/C splits, 2 downstairs, 1 main bedroom, window A/C in bedrooms 2 and 3 standard coffee maker, microwave, toaster, dishwasher Wi-fi and Smart TV (no cable), DVD player Exterior: Outdoor shower, 2 parking spaces, gas grill, patio, sitting areas Other: Dog friendly, no smoking Dennis Rental Registration: RENT-005836-2024 Now Booking 2025

Listed by Chatelain Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Nov 27, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Vacation Rental -- Unforgettable Ocean Front Cottage

2g Beach Hills Road Dennis MA 02639
For Rent

Listing Number X52341337

  • Exclusive Vacation Rentals
  • Village Dennis Port
  • Bathroom 1
  • Bedrooms 2
  • Sleeps 4

  Don't tell your in-laws about this house! You will immediately fall in love with this delightful, warm, and welcoming beach front cottage and you'll never want to stay anywhere else on Cape Cod. From the moment you walk in, you will be charmed by the delightful details throughout the cottage and then you will be stunned by the view overlooking Nantucket Sound.    This 2 bedroom, 1 bath home features so many desirable amenities you will completely forget about once you sit down on the deck, put your feet up, and spend the rest of your vacation gazing at the unobstructed view of the ocean.  But if you end up with a rainy day, you will be completely comfortable in the light and bright home with central A/C and linens provided. The living room features a smart TV with basic cable, DVD player, as well as board games and beach reads for the whole family.  The main bedroom features a queen bed with a view overlooking the deck to the ocean and the cozy second bedroom features two twin beds.  The kitchen is well stocked for basic cooking needs and includes an ice machine and Keurig coffee maker. Worried about lines at the laundromat? No more. Don't lose a second at the beach as this homes comes with a washer and dryer too.     Ready to get your feet wet?  Just off the deck you'll find the stairs to the private association beach down the bluff where you can take a dip or sit and read with the sun warming your face all day.  If you enjoy fishing, the jetties are great spots to catch a striper or just while away the time with your rod and reel.      Time to venture out? Dennis Port village is just 1 mile away where you will find myriad restaurants, bakeries, markets and more. Even closer on Old Wharf Rd and Lower County Rd you can find plenty of dining options and delightful shops too. And just steps away is the Pelham House Resort with an amazing rooftop dining experience.  Stay here and you'll never want to stay anywhere else on Cape Cod. CLICK HERE for up to date pricing and availability Amenities: Private association beach access 2 Bedroom, 1 Bath, Occupancy for 4 Central A/C Linens and bath towels provided Wi-fi, basic cable and smart TV Washer and Dryer Outdoor shower Gas grill Off season availability. May and October 3 nights for $775 and $225 for each additional night (add 14.45% for taxes).  Early June and September 3 nights for $1000 and $300 for each additional night (add 14.45% for taxes).  Dennis Rental Registration: RENT-005991-2024 Now Booking 2025

Listed by Chatelain Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Nov 27, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Vacation Rental -- Water front on Kelley's Pond

97 Fisk Street Dennis MA 02670
For Rent

Listing Number X30990564

  • Exclusive Vacation Rentals
  • Village West Dennis
  • Bathroom 2
  • Maximum Occupants 6
  • Bedrooms 2

This quintessential pond front cottage features walls of windows upstairs surrounding an open-concept living/dining area with serene views of Kelley's Pond.  Wrap-around decks make it easy to relax outside in privacy while enjoying views of the pond.  Swim and play in your back yard, or if you prefer a larger beach, you are less than 1 mile from world-famous West Dennis beach. This home features two bedrooms downstairs each with a queen bed and a day bed that opens into two more twins. The living room has a smart TV so you can bring all your own streaming services. Rinse off in the outdoor shower and watch the sun go down over the pond as you enjoy your new favorite Cape cod vacation spot.   This home is available for 3 night minimums at $250/night for some of the off-season.  Please inquire for details and availability.  For pricing and availability click here Features and Amenities: Linens provided (sheets and bath towels) Bedroom 1 with en-suite half bath and queen bed Bedroom 2 with queen bed Downstairs foyer has day bed with two twins Washer and Dryer Private access to Kelly's Pond (salt water) Outdoor shower Gas grill (propane provided) Smart TV, bring your own streaming services Parking for 2 vehicles Dennis Rental Registration: RENT-006507-2024 Now Booking 2025

Listed by Chatelain Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Nov 27, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Vacation Rental -- 2000ft to Mayflower Beach in Dennis

29 Taunton Avenue Dennis MA 02638
For Rent

Listing Number 29Taun

  • Exclusive Vacation Rentals
  • Village Dennis
  • Bathroom 2
  • Bedrooms 3
  • Type 3 Bedroom Home

Enjoy summer on the Cape at its best! This spacious home is located in charming Dennis Village and is just 2000ft from world-famous Mayflower Beach.  This home features everything you need to make your Cape Cod Vacation a hit: 3 bedrooms with sleeping for 6, central A/C, linens included, gas grill, washer/dryer, a bright living room for relaxing, a cozy den for enjoying your morning coffee, and a large lawn perfect for games and sunbathing. Just getting back from the beach? Rinse off in the outdoor shower and then hang out in the shade   Venture out and enjoy any one of the nearby Dennis Public Beaches, from Chapin to Bayview and of course, nearby Mayflower.  Just over a mile to Dennis Village you'll find popular and local staples such as Dennis Public Market, Cape Cod Creamery, Scargo Cafe, Underground Baker, and The Mercantile, just to name a few. The village also features The Cape Playhouse, a world-class summer theater boasting appearances from the likes of Gregory Peck, Bette Davis and more.  You'll never need to go far to find everything you need in this delightful seaside village while staying at your new favorite Cape Cod vacation home. For up to date pricing and availability click here Off season availability: $2900/week,  3 nights for $1300 each additional night 400 Amenities: Central A/C Washer/Dryer Smart TV (no cable), wifi internet Beds: 1 King, 1 Queen, 1 Double Master Bedroom with ensuite bathroom Dishwasher, standard coffee maker Gas grill Outdoor shower Large yard No pets Non smoking $250 refundable security deposit required Dennis License Number: RENT-005303-2024 Now Booking 2025

Listed by Chatelain Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Nov 27, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Vacation Rental -- Cutie Cottage close to the bike path and hiking trails

17 Gilbert Road Dennis MA 02639
For Rent

Listing Number 17Gil

  • Exclusive Vacation Rentals
  • Village Dennis Port
  • Bathroom 1
  • Maximum Occupants 4
  • Bedrooms 3

Welcome to the Cape! You will fall in love with this lovingly maintained 3 bedroom, 1 bath home in Dennis Port. The main bedroom features a queen bed and window A/C, the second bedroom has twin bunk beds and the third bedroom has a full size futon. Enjoy the new Smart TV and bring all of your own streaming channels. But who wants to spend time inside on vacation? Enjoy the spacious and beautifully maintained yard or take your morning coffee on the deck in the sunshine, or grill up that fish you just caught on the gas grill. Just get back from the beach? Rinse off in the outdoor shower nestled in the bamboo. This home also features a washer and dryer and bed linens and bath towels! Ready to venture out? Dennis Port village is just over .5 mile where you will find myriad shops, restaurants, bakeries, markets and more. This home is also about .5 mile to the Bells Neck Conservation area in Harwich with 259 acres, miles of trails to explore and ponds and rivers to fish and paddle in. Are you a biking enthusiast? Less than a mile is the Cape Cod Rail Trail parking area on Depot St. giving you access to the entire bike trail running from Wellfleet to the newly finished sections in Yarmouth. Buy your own Dennis beach parking pass for a day or the week and enjoy any of the beautiful North or Southside beaches in Town. For up to date pricing and availability click here This home is also available for off-season getaways and is fully heated for a winter retreat. Interior: Washer/dryer, window A/C standard coffee maker, keurig coffee maker, microwave, Wi-fi, Smart TV (no cable), linens provided Exterior: Outdoor shower, 2 parking spaces, gas grill, deck, spacious yard Other: no smoking, no pets Dennis Rental Registration: RENT-005414-2024 Now Booking 2025

Listed by Chatelain Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Nov 27, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Vacation Rental -- Walk 800 feet to Haigis Beach in Dennis

49 Ocean Drive Dennis MA 02639
For Rent

Listing Number X21306544

  • Exclusive Vacation Rentals
  • Village Dennis Port
  • Bathroom 1
  • Maximum Occupants 4
  • Bedrooms 2

This cottage is sure to make your Cape Cod vacation a delight. With a brand new bathroom and numerous updates to the flooring, beds and furniture, this cutie won't disappoint. The light and bright interior makes time spent inside a pleasure - watch the smart TV and relax in the ductless A/C on the love seat. There are 2 bedrooms with a queen in one and a bunked double and twin in the second. Need a little more space? The loveseat also pulls out into a twin. But spend some time outside why don't you. Grill that freshly caught fish with either the charcoal grill or the gas grill. Enjoy the outdoor shower, get some sun on the deck or in the yard with a provided lawn game and take your morning coffee on the serene back patio.    And who can visit the Cape without enjoying the best beaches in Dennis? Haigis Beach is just 800 feet away, Glendon Road Beach less than half a mile, purchase your own daily or weekly Dennis Beach sticker have access to park at any of the other Town beaches. We provide beach chairs and a cooler to make your beach outing a breeze. Fall in love with your new favorite Cape Cod vacation rental.  For up to date pricing and availability click here Amenities:  Interior: A/C ductless split, Microwave, Coffeemaker, Smart TV, Cable TV, DVD, WiFi Exterior: Deck, outdoor shower, stone patio, Charcoal & Gas BBQ grill, outdoor furniture, beach chairs, lawn games, cooler Smoke free Dogs considered, $200/wk additional Off season availability Dennis Rental Registration: RENT-006100-2024 Now Booking 2025

Listed by Chatelain Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Nov 27, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Vacation Rental -- Cape Cutie in West Dennis

107 Swan River Road West Dennis MA 02670
For Rent

Listing Number 107SWAN

  • Exclusive Vacation Rentals
  • Village West Dennis
  • Bathroom 1
  • Maximum Occupants 6
  • Bedrooms 3

This is a consummate Cape Cod rental just over a half mile to South Village Beach in West Dennis. With 3 bedrooms, sleeping for 6, and one full bath, there is plenty of room for everyone (and a laundry in the sunroom too!). The master bedroom has a queen bed with window A/C, the second bedroom has two twin beds, and the third bedroom has two twin beds. The back of the house includes a patio with chairs, a picnic table, as well as a gas grill and an enclosed outdoor shower. The West Dennis area features so many fun local opportunities as well. The home is less than a mile from South Village Beach, just over a mile to West Dennis Beach, and is very close to the Swan River for paddle sports like kayaking, canoeing, and stand up paddle boarding, all of which are rentable close by at Cape Cod Waterways Boat Rentals. Enjoy the local staples of Cape Cod cuisine, Kream 'n Kone less than half a mile away for fried clams, or sandwiches from Holly's Deli just a bit farther. Welcome to Cape Cod! --See here for up to date pricing and availability-- Amenities Include: Wi-Fi Smart TV (no cable) Window A/C in master bedroom only Heat for chilly nights Sunroom with washer and dryer Backyard patio Propane BBQ grill Picnic table Enclosed outdoor shower Parking for 3-4 cars Beds: 1 queen, 4 twin No Pets, No smoking Dennis License Number: 005520-2024 Now Booking 2025

Listed by Chatelain Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Nov 27, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

broker reciprocity The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Chatelain Real Estate are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Chatelain Real Estate shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated December 2, 2024 11:21 PM EST. All properties are subject to prior sale, changes, or withdrawal.

Chatelain Real Estate has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.