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Holiday Homes in South Dennis

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Bedrooms

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59 rentals in South Dennis.
Swan Pond Cottage, Waterfront Central A/C,  Open Floor Plan, holiday rental in South Dennis
Swan Pond Cottage, Waterfront Central A/C,  Open Floor Plan, holiday rental in South Dennis
Swan Pond Cottage, Waterfront Central A/C,  Open Floor Plan, holiday rental in South Dennis

Swan Pond Cottage, Waterfront Central A/C, Open Floor Plan

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Dog friendly home w/ deck and private gas grill - on the bay side of the Cape!, holiday rental in South Dennis
Dog friendly home w/ deck and private gas grill - on the bay side of the Cape!, holiday rental in South Dennis
Dog friendly home w/ deck and private gas grill - on the bay side of the Cape!, holiday rental in South Dennis

Dog friendly home w/ deck and private gas grill - on the bay side of the Cape!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Berry Quaint Cottage, holiday rental in South Dennis
The Berry Quaint Cottage, holiday rental in South Dennis
The Berry Quaint Cottage, holiday rental in South Dennis

The Berry Quaint Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Spacious home with private deck, beach gear, W/D, & central location, holiday rental in South Dennis
Spacious home with private deck, beach gear, W/D, & central location, holiday rental in South Dennis
Spacious home with private deck, beach gear, W/D, & central location, holiday rental in South Dennis

Spacious home with private deck, beach gear, W/D, & central location

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Freydis Glen | Dog-friendly cottage in South Dennis with firepit - walk to bay, holiday rental in South Dennis
Freydis Glen | Dog-friendly cottage in South Dennis with firepit - walk to bay, holiday rental in South Dennis
Freydis Glen | Dog-friendly cottage in South Dennis with firepit - walk to bay, holiday rental in South Dennis

Freydis Glen | Dog-friendly cottage in South Dennis with firepit - walk to bay

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Thayer Thicket | Newly renovated house in South Dennis with great location, holiday rental in South Dennis
Thayer Thicket | Newly renovated house in South Dennis with great location, holiday rental in South Dennis
Thayer Thicket | Newly renovated house in South Dennis with great location, holiday rental in South Dennis

Thayer Thicket | Newly renovated house in South Dennis with great location

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Modern, clean and cozy home away from home, holiday rental in South Dennis
Modern, clean and cozy home away from home, holiday rental in South Dennis
Modern, clean and cozy home away from home, holiday rental in South Dennis

Modern, clean and cozy home away from home

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Home Away From Home, holiday rental in South Dennis
Home Away From Home, holiday rental in South Dennis
Home Away From Home, holiday rental in South Dennis

Home Away From Home

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Centrally located 2 bedroom Ranch in Dennis, holiday rental in South Dennis
Centrally located 2 bedroom Ranch in Dennis, holiday rental in South Dennis
Centrally located 2 bedroom Ranch in Dennis, holiday rental in South Dennis

Centrally located 2 bedroom Ranch in Dennis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spectacular newly renovated 3 bedroom- Bayside neighborhood close to beaches, holiday rental in South Dennis
Spectacular newly renovated 3 bedroom- Bayside neighborhood close to beaches, holiday rental in South Dennis
Spectacular newly renovated 3 bedroom- Bayside neighborhood close to beaches, holiday rental in South Dennis

Spectacular newly renovated 3 bedroom- Bayside neighborhood close to beaches

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Petite beach home overlooking Follins Pond w/ central A/C and private gas grill!, holiday rental in South Dennis
Petite beach home overlooking Follins Pond w/ central A/C and private gas grill!, holiday rental in South Dennis
Petite beach home overlooking Follins Pond w/ central A/C and private gas grill!, holiday rental in South Dennis

Petite beach home overlooking Follins Pond w/ central A/C and private gas grill!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Lovely Cottage With Private Yard Convenient to Dennis Shopping and Dining, holiday rental in South Dennis
Lovely Cottage With Private Yard Convenient to Dennis Shopping and Dining, holiday rental in South Dennis
Lovely Cottage With Private Yard Convenient to Dennis Shopping and Dining, holiday rental in South Dennis

Lovely Cottage With Private Yard Convenient to Dennis Shopping and Dining

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Pet Friendly , Perfect Price, House and Spot, holiday rental in South Dennis
Pet Friendly , Perfect Price, House and Spot, holiday rental in South Dennis
Pet Friendly , Perfect Price, House and Spot, holiday rental in South Dennis

Pet Friendly , Perfect Price, House and Spot

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Great location to everything 5 mins to some of the best beaches fenced in yard, holiday rental in South Dennis
Great location to everything 5 mins to some of the best beaches fenced in yard, holiday rental in South Dennis
Great location to everything 5 mins to some of the best beaches fenced in yard, holiday rental in South Dennis

Great location to everything 5 mins to some of the best beaches fenced in yard

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Family Friendly Mid Cape Home • Sleeps 6 • Steps to Kelly Bay • Near Beaches, holiday rental in South Dennis
Family Friendly Mid Cape Home • Sleeps 6 • Steps to Kelly Bay • Near Beaches, holiday rental in South Dennis
Family Friendly Mid Cape Home • Sleeps 6 • Steps to Kelly Bay • Near Beaches, holiday rental in South Dennis

Family Friendly Mid Cape Home • Sleeps 6 • Steps to Kelly Bay • Near Beaches

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Spectacular three bedroom home with central air, holiday rental in South Dennis
Spectacular three bedroom home with central air, holiday rental in South Dennis
Spectacular three bedroom home with central air, holiday rental in South Dennis

Spectacular three bedroom home with central air

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Escape to the Cape in this brand new, family-friendly, centrally located home., holiday rental in South Dennis
Escape to the Cape in this brand new, family-friendly, centrally located home., holiday rental in South Dennis
Escape to the Cape in this brand new, family-friendly, centrally located home., holiday rental in South Dennis

Escape to the Cape in this brand new, family-friendly, centrally located home.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Idyllic 3BR classic Cape Cottage in a beautiful waterfront setting, with sunsets, holiday rental in South Dennis
Idyllic 3BR classic Cape Cottage in a beautiful waterfront setting, with sunsets, holiday rental in South Dennis
Idyllic 3BR classic Cape Cottage in a beautiful waterfront setting, with sunsets, holiday rental in South Dennis

Idyllic 3BR classic Cape Cottage in a beautiful waterfront setting, with sunsets

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Cape Cod House, holiday rental in South Dennis
Cape Cod House, holiday rental in South Dennis
Cape Cod House, holiday rental in South Dennis

Cape Cod House

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Grand Cove Retreat, holiday rental in South Dennis
Grand Cove Retreat, holiday rental in South Dennis
Grand Cove Retreat, holiday rental in South Dennis

Grand Cove Retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Three bedroom home sleeping 8 overlooking Swan Pond, holiday rental in South Dennis
Three bedroom home sleeping 8 overlooking Swan Pond, holiday rental in South Dennis
Three bedroom home sleeping 8 overlooking Swan Pond, holiday rental in South Dennis

Three bedroom home sleeping 8 overlooking Swan Pond

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Sea Gem Hideaway | House in South Dennis in a prime location w/ outdoor shower, holiday rental in South Dennis
Sea Gem Hideaway | House in South Dennis in a prime location w/ outdoor shower, holiday rental in South Dennis
Sea Gem Hideaway | House in South Dennis in a prime location w/ outdoor shower, holiday rental in South Dennis

Sea Gem Hideaway | House in South Dennis in a prime location w/ outdoor shower

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Newly Updated Home Stone Patio & Fire Pit!, holiday rental in South Dennis
Newly Updated Home Stone Patio & Fire Pit!, holiday rental in South Dennis
Newly Updated Home Stone Patio & Fire Pit!, holiday rental in South Dennis

Newly Updated Home Stone Patio & Fire Pit!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Lovely three bedroom home located in desirable Bayside neighborhood!, holiday rental in South Dennis
Lovely three bedroom home located in desirable Bayside neighborhood!, holiday rental in South Dennis
Lovely three bedroom home located in desirable Bayside neighborhood!, holiday rental in South Dennis

Lovely three bedroom home located in desirable Bayside neighborhood!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Conveniently Located in the heart of Dennis 3 bedroom 1.5 bath with Central Air, holiday rental in South Dennis
Conveniently Located in the heart of Dennis 3 bedroom 1.5 bath with Central Air, holiday rental in South Dennis
Conveniently Located in the heart of Dennis 3 bedroom 1.5 bath with Central Air, holiday rental in South Dennis

Conveniently Located in the heart of Dennis 3 bedroom 1.5 bath with Central Air

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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3 bedroom home with ac, holiday rental in South Dennis
3 bedroom home with ac, holiday rental in South Dennis
3 bedroom home with ac, holiday rental in South Dennis

3 bedroom home with ac

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Newly Updated Home Stone Patio & Fire Pit!, holiday rental in South Dennis
Newly Updated Home Stone Patio & Fire Pit!, holiday rental in South Dennis
Newly Updated Home Stone Patio & Fire Pit!, holiday rental in South Dennis

Newly Updated Home Stone Patio & Fire Pit!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Walk to Harborview Beach, holiday rental in South Dennis
Walk to Harborview Beach, holiday rental in South Dennis
Walk to Harborview Beach, holiday rental in South Dennis

Walk to Harborview Beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful, bright, and airy home located in scenic Quivet Neck, East Dennis, holiday rental in South Dennis
Beautiful, bright, and airy home located in scenic Quivet Neck, East Dennis, holiday rental in South Dennis
Beautiful, bright, and airy home located in scenic Quivet Neck, East Dennis, holiday rental in South Dennis

Beautiful, bright, and airy home located in scenic Quivet Neck, East Dennis

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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New to our 2023 Inventory!  Spectacular three bedroom home with central air, holiday rental in South Dennis
New to our 2023 Inventory!  Spectacular three bedroom home with central air, holiday rental in South Dennis
New to our 2023 Inventory!  Spectacular three bedroom home with central air, holiday rental in South Dennis

New to our 2023 Inventory! Spectacular three bedroom home with central air

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Spectacular newly renovated 3 bedroom- Bayside neighborhood close to beaches, holiday rental in South Dennis
Spectacular newly renovated 3 bedroom- Bayside neighborhood close to beaches, holiday rental in South Dennis
Spectacular newly renovated 3 bedroom- Bayside neighborhood close to beaches, holiday rental in South Dennis

Spectacular newly renovated 3 bedroom- Bayside neighborhood close to beaches

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Three bedroom home sleeping 8 on the water's edge of Swan River, holiday rental in South Dennis
Three bedroom home sleeping 8 on the water's edge of Swan River, holiday rental in South Dennis
Three bedroom home sleeping 8 on the water's edge of Swan River, holiday rental in South Dennis

Three bedroom home sleeping 8 on the water's edge of Swan River

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private Dock! 3 bedroom, 2 bath home-directly on Swan River, holiday rental in South Dennis
Private Dock! 3 bedroom, 2 bath home-directly on Swan River, holiday rental in South Dennis
Private Dock! 3 bedroom, 2 bath home-directly on Swan River, holiday rental in South Dennis

Private Dock! 3 bedroom, 2 bath home-directly on Swan River

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Amazing pond views and unforgettable sunsets from all levels, holiday rental in South Dennis
Amazing pond views and unforgettable sunsets from all levels, holiday rental in South Dennis
Amazing pond views and unforgettable sunsets from all levels, holiday rental in South Dennis

Amazing pond views and unforgettable sunsets from all levels

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Short Walk to Swan Pond, Hot Tub!, holiday rental in South Dennis
Short Walk to Swan Pond, Hot Tub!, holiday rental in South Dennis
Short Walk to Swan Pond, Hot Tub!, holiday rental in South Dennis

Short Walk to Swan Pond, Hot Tub!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Pristine condition! Three bedroom sleeping 8 with contemporary beach decor!, holiday rental in South Dennis
Pristine condition! Three bedroom sleeping 8 with contemporary beach decor!, holiday rental in South Dennis
Pristine condition! Three bedroom sleeping 8 with contemporary beach decor!, holiday rental in South Dennis

Pristine condition! Three bedroom sleeping 8 with contemporary beach decor!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful Waterfront-Relaxin' on the River!, holiday rental in South Dennis
Beautiful Waterfront-Relaxin' on the River!, holiday rental in South Dennis
Beautiful Waterfront-Relaxin' on the River!, holiday rental in South Dennis

Beautiful Waterfront-Relaxin' on the River!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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3 bedroom home with ac, holiday rental in South Dennis
3 bedroom home with ac, holiday rental in South Dennis
3 bedroom home with ac, holiday rental in South Dennis

3 bedroom home with ac

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Pristine condition! Three bedroom sleeping 10 with contemporary beach decor!, holiday rental in South Dennis
Pristine condition! Three bedroom sleeping 10 with contemporary beach decor!, holiday rental in South Dennis
Pristine condition! Three bedroom sleeping 10 with contemporary beach decor!, holiday rental in South Dennis

Pristine condition! Three bedroom sleeping 10 with contemporary beach decor!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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New to our 2023 inventory!  Grand Cove Retreat, holiday rental in South Dennis
New to our 2023 inventory!  Grand Cove Retreat, holiday rental in South Dennis
New to our 2023 inventory!  Grand Cove Retreat, holiday rental in South Dennis

New to our 2023 inventory! Grand Cove Retreat

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Amazing pond views and unforgettable sunsets from all levels, holiday rental in South Dennis
Amazing pond views and unforgettable sunsets from all levels, holiday rental in South Dennis
Amazing pond views and unforgettable sunsets from all levels, holiday rental in South Dennis

Amazing pond views and unforgettable sunsets from all levels

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Raised Split Ranch Single House in South Dennis., holiday rental in South Dennis
Raised Split Ranch Single House in South Dennis., holiday rental in South Dennis
Raised Split Ranch Single House in South Dennis., holiday rental in South Dennis

Raised Split Ranch Single House in South Dennis.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Three bedroom home with central air conditioning, holiday rental in South Dennis
Three bedroom home with central air conditioning, holiday rental in South Dennis
Three bedroom home with central air conditioning, holiday rental in South Dennis

Three bedroom home with central air conditioning

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Short walk to Sesuit Harbor, holiday rental in South Dennis
Short walk to Sesuit Harbor, holiday rental in South Dennis
Short walk to Sesuit Harbor, holiday rental in South Dennis

Short walk to Sesuit Harbor

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Pristine Vacation Home on Aunt Patty's Pond, holiday rental in South Dennis
Pristine Vacation Home on Aunt Patty's Pond, holiday rental in South Dennis
Pristine Vacation Home on Aunt Patty's Pond, holiday rental in South Dennis

Pristine Vacation Home on Aunt Patty's Pond

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private Pool, Large Deck, and Game Room!, holiday rental in South Dennis
Private Pool, Large Deck, and Game Room!, holiday rental in South Dennis
Private Pool, Large Deck, and Game Room!, holiday rental in South Dennis

Private Pool, Large Deck, and Game Room!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Gorgeous Getaway on the Cape Cod Bikepath **New!**, holiday rental in South Dennis
Gorgeous Getaway on the Cape Cod Bikepath **New!**, holiday rental in South Dennis
Gorgeous Getaway on the Cape Cod Bikepath **New!**, holiday rental in South Dennis

Gorgeous Getaway on the Cape Cod Bikepath **New!**

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Bayside five bedroom sleeping 10 with central air, holiday rental in South Dennis
Bayside five bedroom sleeping 10 with central air, holiday rental in South Dennis
Bayside five bedroom sleeping 10 with central air, holiday rental in South Dennis

Bayside five bedroom sleeping 10 with central air

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Kelly's Bay House - Short walk to Kelly's Bay and Public Park - 16 Town Beaches, holiday rental in South Dennis
Kelly's Bay House - Short walk to Kelly's Bay and Public Park - 16 Town Beaches, holiday rental in South Dennis
Kelly's Bay House - Short walk to Kelly's Bay and Public Park - 16 Town Beaches, holiday rental in South Dennis

Kelly's Bay House - Short walk to Kelly's Bay and Public Park - 16 Town Beaches

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Dog-friendly 4 bedroom 4 bathroom sleeps 10 home near bay side beaches and, holiday rental in South Dennis
Dog-friendly 4 bedroom 4 bathroom sleeps 10 home near bay side beaches and, holiday rental in South Dennis
Dog-friendly 4 bedroom 4 bathroom sleeps 10 home near bay side beaches and, holiday rental in South Dennis

Dog-friendly 4 bedroom 4 bathroom sleeps 10 home near bay side beaches and

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Showing results 1-50 of 59
Frequently Asked Questions about South Dennis