Vacation rentals in Tolchester Beach, MD

48 available vacation rental offers

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Best vacation rentals and Airbnb offers in Tolchester Beach, MD

Studio apartment in water view Historic home with WiFi, separate AC/heat - Tolchester Beach, MD

Studio apartment in water view Historic home with WiFi, separate AC/heat

Apartment, Tolchester Beach

Studio apartment in water view Historic home with WiFi, separate AC/heat is a apartment in Tolchester Beach, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Studio apartment in water view Historic home with WiFi, separate AC/heat

Studio apartment in water view Historic home with WiFi, separate AC/heat is a apartment in Tolchester Beach, with 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $834.

From$119/night
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3 Mi to Washington College! Updated Home w/ Patio - Tolchester Beach, MD

3 Mi to Washington College! Updated Home w/ Patio

Cottage, Tolchester Beach

3 Mi to Washington College! Updated Home w/ Patio is a cottage in Tolchester Beach, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 3 Mi to Washington College! Updated Home w/ Patio

3 Mi to Washington College! Updated Home w/ Patio is a cottage in Tolchester Beach, with outdoor 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,421.

From$135/night
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3 Mi to Washington College! Updated Home w/ Patio - Tolchester Beach, MD

3 Mi to Washington College! Updated Home w/ Patio

Holiday Home, Tolchester Beach

3 Mi to Washington College! Updated Home w/ Patio is a holiday home in Tolchester Beach, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 3 Mi to Washington College! Updated Home w/ Patio

3 Mi to Washington College! Updated Home w/ Patio is a holiday home in Tolchester Beach, with outdoor 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,212.

From$173/night
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Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! - Tolchester Beach, MD

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment, Tolchester Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! is a apartment in Tolchester Beach, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! is a apartment in Tolchester Beach, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,249.

From$178/night
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Waterfront vacation rentals in Tolchester Beach, MD

Discover vacation rentals close to the coast, water, and beach areas around Tolchester Beach, MD.

Beachcomber Suite - Tolchester Beach, MD

Beachcomber Suite

Apartment, Tolchester Beach

Beachcomber Suite is a apartment in Tolchester Beach, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Beachcomber Suite

Beachcomber Suite is a apartment in Tolchester Beach, with 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,331.

From$190/night
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Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River - Tolchester Beach, MD

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River

Apartment, Tolchester Beach

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River is a apartment in Tolchester Beach, with parking, kitchen access, and room for a group. This stay gives…

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About Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River is a apartment in Tolchester Beach, 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 $1,861.

From$266/night
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Quiet Bird River Bungalow and Nature Retreat Pet Friendly - Tolchester Beach, MD

Quiet Bird River Bungalow and Nature Retreat Pet Friendly

Holiday Home, Tolchester Beach

Quiet Bird River Bungalow and Nature Retreat Pet Friendly is a holiday home in Tolchester Beach, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a…

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About Quiet Bird River Bungalow and Nature Retreat Pet Friendly

Quiet Bird River Bungalow and Nature Retreat Pet Friendly is a holiday home in Tolchester Beach, with pet-friendly space, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,138.

From$305/night
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Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore! - Tolchester Beach, MD

Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore!

Holiday Home, Tolchester Beach

Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore! is a holiday home in Tolchester Beach, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore!

Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore! is a holiday home in Tolchester Beach, with easy beach access, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,998.

From$428/night
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Vacation rentals with a pool in Tolchester Beach, MD

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

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. - Tolchester Beach, MD

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

Holiday Home, Tolchester Beach

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. is a holiday home in Tolchester Beach, with pool access, easy beach access, and kitchen access. This stay…

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About A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. is a holiday home in Tolchester Beach, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,223.

From$1,175/night
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Historic Manor House on Beautiful Eastern Shore Estate - Tolchester Beach, MD

Historic Manor House on Beautiful Eastern Shore Estate

Holiday Home, Tolchester Beach

Historic Manor House on Beautiful Eastern Shore Estate is a holiday home in Tolchester Beach, with pet-friendly space and pool access. This stay gives travelers a comfortable base for…

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About Historic Manor House on Beautiful Eastern Shore Estate

Historic Manor House on Beautiful Eastern Shore Estate is a holiday home in Tolchester Beach, with pet-friendly space and 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, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,219.

From$1,317/night
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Inn at Huntingfield Creek - Tolchester Beach, MD

Inn at Huntingfield Creek

B & B, Tolchester Beach

Inn at Huntingfield Creek is a b & b in Tolchester Beach, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Inn at Huntingfield Creek

Inn at Huntingfield Creek is a b & b in Tolchester Beach, 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, free wifi, and for couples.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,497.

From$320/night
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Inn at Huntingfield Creek - Tolchester Beach, MD

Inn at Huntingfield Creek

B & B, Tolchester Beach

Inn at Huntingfield Creek is a b & b in Tolchester Beach, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Inn at Huntingfield Creek

Inn at Huntingfield Creek is a b & b in Tolchester Beach, 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 breakfast, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,490.

From$320/night
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Vacation rentals with parking in Tolchester Beach, MD

Find vacation rentals that make arriving by car easier.

Newly restored apartment in the heart of Chestertown - Tolchester Beach, MD

Newly restored apartment in the heart of Chestertown

Apartment, Tolchester Beach

Newly restored apartment in the heart of Chestertown is a apartment in Tolchester Beach, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown is a apartment in Tolchester Beach, with 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,026.

From$289/night
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Circa 1900 Home in the Heart of Historic Downtown Chestertown - Tolchester Beach, MD

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Holiday Home, Tolchester Beach

Circa 1900 Home in the Heart of Historic Downtown Chestertown is a holiday home in Tolchester Beach, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Circa 1900 Home in the Heart of Historic Downtown Chestertown

Circa 1900 Home in the Heart of Historic Downtown Chestertown is a holiday home in Tolchester Beach, with 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,213.

From$316/night
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Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall - Tolchester Beach, MD

Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall

Holiday Home, Tolchester Beach

Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall is a holiday home in Tolchester Beach, with parking and room for a group. This stay gives travelers a comfortable…

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About Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall

Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall is a holiday home in Tolchester Beach, with parking 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, parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,244.

From$321/night
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Brampton 1860 - Tolchester Beach, MD

Brampton 1860

B & B, Tolchester Beach

Brampton 1860 is a b & b in Tolchester Beach, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Brampton 1860

Brampton 1860 is a b & b in Tolchester Beach, with 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 breakfast, free wifi, parking, paid parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,978.

From$383/night
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Pet-friendly vacation rentals in Tolchester Beach, MD

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

200 steps to the beach! - Tolchester Beach, MD

200 steps to the beach!

Holiday Home, Tolchester Beach

200 steps to the beach! is a holiday home in Tolchester Beach, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area,…

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About 200 steps to the beach!

200 steps to the beach! is a holiday home in Tolchester Beach, 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 $2,236.

From$319/night
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Bayside Cottage steps from Rock Hall Harbor - Tolchester Beach, MD

Bayside Cottage steps from Rock Hall Harbor

Holiday Home, Tolchester Beach

Bayside Cottage steps from Rock Hall Harbor is a holiday home in Tolchester Beach, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor is a holiday home in Tolchester Beach, 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 $2,330.

From$333/night
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Serene Waterfront Cottage with dock and gorgeous views. - Tolchester Beach, MD

Serene Waterfront Cottage with dock and gorgeous views.

Holiday Home, Tolchester Beach

Serene Waterfront Cottage with dock and gorgeous views. is a holiday home in Tolchester Beach, with pet-friendly space, easy beach access, and parking. This stay gives travelers a…

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About Serene Waterfront Cottage with dock and gorgeous views.

Serene Waterfront Cottage with dock and gorgeous views. is a holiday home in Tolchester Beach, 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 $2,390.

From$341/night
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Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town. - Tolchester Beach, MD

Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town.

Holiday Home, Tolchester Beach

Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town. is a holiday home in Tolchester Beach, with pet-friendly space. This stay gives travelers a comfortable base…

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About Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town.

Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town. is a holiday home in Tolchester Beach, 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 $2,946.

From$421/night
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Vacation rentals with a kitchen in Tolchester Beach, MD

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

Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio - Tolchester Beach, MD

Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio

Holiday Home, Tolchester Beach

Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio is a holiday home in Tolchester Beach, with easy beach access, outdoor space, and parking. This stay gives travelers…

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About Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio

Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio is a holiday home in Tolchester Beach, with easy beach access, outdoor space, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,498.

From$357/night
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EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home - Tolchester Beach, MD

EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home

Holiday Home, Tolchester Beach

EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home is a holiday home in Tolchester Beach, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home

EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home is a holiday home in Tolchester Beach, 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 $2,604.

From$372/night
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Newly renovated single family home with attached guest suite - Tolchester Beach, MD

Newly renovated single family home with attached guest suite

Holiday Home, Tolchester Beach

Newly renovated single family home with attached guest suite is a holiday home in Tolchester Beach, with kitchen access and room for a group. This stay gives travelers a comfortable base…

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About Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite is a holiday home in Tolchester Beach, with 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 $2,675.

From$382/night
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Beautiful, spacious, quiet waterfront house! - Tolchester Beach, MD

Beautiful, spacious, quiet waterfront house!

Holiday Home, Tolchester Beach

Beautiful, spacious, quiet waterfront house! is a holiday home in Tolchester Beach, with easy beach access, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

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About Beautiful, spacious, quiet waterfront house!

Beautiful, spacious, quiet waterfront house! is a holiday home in Tolchester Beach, with easy beach access, 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: hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,727.

From$390/night
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