Vacation rentals in Big Pond, MD

62 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Big Pond, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Big Pond, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Big Pond

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Big Pond, with easy beach access, parking, and a quieter setting. This stay gives travelers a comfortable base for…

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About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Big Pond, with easy beach access, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,684.

From$150/night
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'callaway Drive Retreat' 3BR Home Near Water - Big Pond, MD

'callaway Drive Retreat' 3BR Home Near Water

Cottage, Big Pond

'callaway Drive Retreat' 3BR Home Near Water is a cottage in Big Pond, with kitchen access, room for a group, and a quieter setting. This stay gives travelers a comfortable base for…

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About 'callaway Drive Retreat' 3BR Home Near Water

'callaway Drive Retreat' 3BR Home Near Water is a cottage in Big Pond, with kitchen access, room for a group, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,747.

From$184/night
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Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis - Big Pond, MD

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Apartment, Big Pond

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis is a apartment in Big Pond, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis is a apartment in Big Pond, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,328.

From$190/night
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Charming 1-bedroom cottage with AC in cozy Harwood - Big Pond, MD

Charming 1-bedroom cottage with AC in cozy Harwood

Cottage, Big Pond

Charming 1-bedroom cottage with AC in cozy Harwood is a cottage in Big Pond, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Charming 1-bedroom cottage with AC in cozy Harwood

Charming 1-bedroom cottage with AC in cozy Harwood is a cottage in Big Pond, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,337.

From$191/night
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Browse Vacation Rentals with a Pool in Big Pond, MD

Add a pool to the search when you want an easy place to cool off between outings.

Modern Bay Dream - Big Pond, MD

Modern Bay Dream

Holiday Home, Big Pond

Modern Bay Dream is a holiday home in Big Pond, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Modern Bay Dream

Modern Bay Dream is a holiday home in Big Pond, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,156.

From$594/night
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42 Acres of Serenity & Nature Just 15 Miles To Annapolis - Big Pond, MD

42 Acres of Serenity & Nature Just 15 Miles To Annapolis

Holiday Home, Big Pond

42 Acres of Serenity & Nature Just 15 Miles To Annapolis is a holiday home in Big Pond, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 42 Acres of Serenity & Nature Just 15 Miles To Annapolis

42 Acres of Serenity & Nature Just 15 Miles To Annapolis is a holiday home in Big Pond, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,917.

From$988/night
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USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR - Big Pond, MD

USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

Holiday Home, Big Pond

USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR is a holiday home in Big Pond, with pool access and kitchen access. This stay gives travelers a comfortable…

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About USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR is a holiday home in Big Pond, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,041.

From$1,006/night
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The Inn at Tacaro Estate - Big Pond, MD

The Inn at Tacaro Estate

B & B, Big Pond

The Inn at Tacaro Estate is a b & b in Big Pond, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About The Inn at Tacaro Estate

The Inn at Tacaro Estate is a b & b in Big Pond, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free breakfast, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,583.

From$449/night
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Best Big Pond, MD vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Relax on Kent Island in a 4 Bedroom Home w/Waterview! - Big Pond, MD

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Holiday Home, Big Pond

Relax on Kent Island in a 4 Bedroom Home w/Waterview! is a holiday home in Big Pond, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview! is a holiday home in Big Pond, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,378.

From$340/night
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2BR Historic District Gem w/Parking Near City Dock - Big Pond, MD

2BR Historic District Gem w/Parking Near City Dock

Holiday Home, Big Pond

2BR Historic District Gem w/Parking Near City Dock is a holiday home in Big Pond, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 2BR Historic District Gem w/Parking Near City Dock

2BR Historic District Gem w/Parking Near City Dock is a holiday home in Big Pond, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,801.

From$400/night
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Enchanting West River Retreat - Big Pond, MD

Enchanting West River Retreat

Cottage, Big Pond

Enchanting West River Retreat is a cottage in Big Pond, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Enchanting West River Retreat

Enchanting West River Retreat is a cottage in Big Pond, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,905.

From$415/night
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Port of Call: 5BR Modern Nautical Luxury - Big Pond, MD

Port of Call: 5BR Modern Nautical Luxury

Holiday Home, Big Pond

Port of Call: 5BR Modern Nautical Luxury is a holiday home in Big Pond, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Port of Call: 5BR Modern Nautical Luxury

Port of Call: 5BR Modern Nautical Luxury is a holiday home in Big Pond, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,513.

From$502/night
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Best Pet-Friendly Vacation Rentals in Big Pond, MD

Bring your pet along with stays that welcome four-legged travelers.

Charming cottage along water with private pier, near St. Michaels Winery - Big Pond, MD

Charming cottage along water with private pier, near St. Michaels Winery

Cottage, Big Pond

Charming cottage along water with private pier, near St. Michaels Winery is a cottage in Big Pond, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Charming cottage along water with private pier, near St. Michaels Winery

Charming cottage along water with private pier, near St. Michaels Winery is a cottage in Big Pond, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,991.

From$284/night
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Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK - Big Pond, MD

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Cottage, Big Pond

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK is a cottage in Big Pond, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK is a cottage in Big Pond, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,292.

From$327/night
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Pet Friendly Hideaway for 4 Close to Annapolis - Big Pond, MD

Pet Friendly Hideaway for 4 Close to Annapolis

Holiday Home, Big Pond

Pet Friendly Hideaway for 4 Close to Annapolis is a holiday home in Big Pond, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Pet Friendly Hideaway for 4 Close to Annapolis

Pet Friendly Hideaway for 4 Close to Annapolis is a holiday home in Big Pond, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,651.

From$379/night
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Sunny and spacious water view/access home in Annapolis. - Big Pond, MD

Sunny and spacious water view/access home in Annapolis.

Holiday Home, Big Pond

Sunny and spacious water view/access home in Annapolis. is a holiday home in Big Pond, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Sunny and spacious water view/access home in Annapolis.

Sunny and spacious water view/access home in Annapolis. is a holiday home in Big Pond, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,739.

From$534/night
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Best Big Pond, MD vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay - Big Pond, MD

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay

Holiday Home, Big Pond

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay is a holiday home in Big Pond, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Chic 3 BR / 2 BA Cottage Near Chesapeake Bay

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay is a holiday home in Big Pond, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,420.

From$346/night
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Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy. - Big Pond, MD

Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy.

Holiday Home, Big Pond

Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy. is a holiday home in Big Pond, with pet-friendly space, kitchen access, and room for a group. This stay gives…

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About Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy.

Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy. is a holiday home in Big Pond, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,186.

From$598/night
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Ahoy! Game Room, Screened Porch, Yard Mins to DTA - Big Pond, MD

Ahoy! Game Room, Screened Porch, Yard Mins to DTA

Holiday Home, Big Pond

Ahoy! Game Room, Screened Porch, Yard Mins to DTA is a holiday home in Big Pond, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Ahoy! Game Room, Screened Porch, Yard Mins to DTA

Ahoy! Game Room, Screened Porch, Yard Mins to DTA is a holiday home in Big Pond, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,260.

From$609/night
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6BR 3 Bath Waterfront Home w/ Private Dock & Views - Big Pond, MD

6BR 3 Bath Waterfront Home w/ Private Dock & Views

Holiday Home, Big Pond

6BR 3 Bath Waterfront Home w/ Private Dock & Views is a holiday home in Big Pond, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About 6BR 3 Bath Waterfront Home w/ Private Dock & Views

6BR 3 Bath Waterfront Home w/ Private Dock & Views is a holiday home in Big Pond, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, gym, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,084.

From$726/night
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Our Favorite Family-Friendly Vacation Rentals in Big Pond, MD

Plan a trip with stays that give families more room to spread out.

Updated North Beach Cottage: Pet Friendly! - Big Pond, MD

Updated North Beach Cottage: Pet Friendly!

Holiday Home, Big Pond

Updated North Beach Cottage: Pet Friendly! is a holiday home in Big Pond, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

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About Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly! is a holiday home in Big Pond, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,974.

From$195/night
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Updated North Beach Cottage: Pet Friendly! - Big Pond, MD

Updated North Beach Cottage: Pet Friendly!

Cottage, Big Pond

Updated North Beach Cottage: Pet Friendly! is a cottage in Big Pond, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the…

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About Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly! is a cottage in Big Pond, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,660.

From$237/night
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Updated North Beach Cottage: Pet Friendly! - Big Pond, MD

Updated North Beach Cottage: Pet Friendly!

Cottage, Big Pond

Updated North Beach Cottage: Pet Friendly! is a cottage in Big Pond, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly! is a cottage in Big Pond, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,291.

From$261/night
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Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach - Big Pond, MD

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Holiday Home, Big Pond

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach is a holiday home in Big Pond, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach is a holiday home in Big Pond, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,630.

From$661/night
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