Vacation rentals in Winchester-on-the-Severn, MD

77 available vacation rental offers

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Best vacation rentals and Airbnb offers in Winchester-on-the-Severn, MD

Charming house with WiFi, fitness room, AC in brilliant Severn - Winchester-on-the-Severn, MD

Charming house with WiFi, fitness room, AC in brilliant Severn

Holiday Home, Winchester-on-the-Severn

Charming house with WiFi, fitness room, AC in brilliant Severn is a holiday home in Winchester-on-the-Severn, with kitchen access. This stay gives travelers a comfortable base for exploring…

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About Charming house with WiFi, fitness room, AC in brilliant Severn

Charming house with WiFi, fitness room, AC in brilliant Severn is a holiday home in Winchester-on-the-Severn, with 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $697.

From$100/night
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Delightful 1-bed 1 bath studio with AC/Heat near BWI - Winchester-on-the-Severn, MD

Delightful 1-bed 1 bath studio with AC/Heat near BWI

Apartment, Winchester-on-the-Severn

Delightful 1-bed 1 bath studio with AC/Heat near BWI is a apartment in Winchester-on-the-Severn, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Delightful 1-bed 1 bath studio with AC/Heat near BWI

Delightful 1-bed 1 bath studio with AC/Heat near BWI is a apartment in Winchester-on-the-Severn, with 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $706.

From$101/night
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Spacious Private Basement - Winchester-on-the-Severn, MD

Spacious Private Basement

Holiday Home, Winchester-on-the-Severn

Spacious Private Basement is a holiday home in Winchester-on-the-Severn, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Spacious Private Basement

Spacious Private Basement is a holiday home in Winchester-on-the-Severn, 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 $907.

From$130/night
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Cozy 1-bedroom studio in pleasant Crofton with AC - Winchester-on-the-Severn, MD

Cozy 1-bedroom studio in pleasant Crofton with AC

Apartment, Winchester-on-the-Severn

Cozy 1-bedroom studio in pleasant Crofton with AC is a apartment in Winchester-on-the-Severn, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Cozy 1-bedroom studio in pleasant Crofton with AC

Cozy 1-bedroom studio in pleasant Crofton with AC is a apartment in Winchester-on-the-Severn, 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, gym, and parking.

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

From$143/night
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Vacation rentals with a pool in Winchester-on-the-Severn, MD

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

BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck - Winchester-on-the-Severn, MD

BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck

Holiday Home, Winchester-on-the-Severn

BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck is a holiday home in Winchester-on-the-Severn, with pool access, outdoor space, and room for a group. This…

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About BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck

BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck is a holiday home in Winchester-on-the-Severn, with pool access, outdoor space, 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,228.

From$461/night
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HiddenParadise in Scenic community, mins to attractions & WaterFront. Sleeps 9 - Winchester-on-the-Severn, MD

HiddenParadise in Scenic community, mins to attractions & WaterFront. Sleeps 9

Holiday Home, Winchester-on-the-Severn

HiddenParadise in Scenic community, mins to attractions & WaterFront. Sleeps 9 is a holiday home in Winchester-on-the-Severn, with pet-friendly space, pool access, and easy beach access.…

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About HiddenParadise in Scenic community, mins to attractions & WaterFront. Sleeps 9

HiddenParadise in Scenic community, mins to attractions & WaterFront. Sleeps 9 is a holiday home in Winchester-on-the-Severn, with pet-friendly space, 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,830.

From$547/night
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USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR - Winchester-on-the-Severn, MD

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

Holiday Home, Winchester-on-the-Severn

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

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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 Winchester-on-the-Severn, 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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Chesapeake Bay Waterfront ARTectural Home - Winchester-on-the-Severn, MD

Chesapeake Bay Waterfront ARTectural Home

Holiday Home, Winchester-on-the-Severn

Chesapeake Bay Waterfront ARTectural Home is a holiday home in Winchester-on-the-Severn, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring…

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About Chesapeake Bay Waterfront ARTectural Home

Chesapeake Bay Waterfront ARTectural Home is a holiday home in Winchester-on-the-Severn, 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 $8,130.

From$1,161/night
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Vacation rentals with parking in Winchester-on-the-Severn, MD

Find vacation rentals that make arriving by car easier.

Stunning 2-Bedroom loft apartment in waterfront community near BWI - Winchester-on-the-Severn, MD

Stunning 2-Bedroom loft apartment in waterfront community near BWI

Apartment, Winchester-on-the-Severn

Stunning 2-Bedroom loft apartment in waterfront community near BWI is a apartment in Winchester-on-the-Severn, with pet-friendly space, easy beach access, and parking. This stay gives…

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About Stunning 2-Bedroom loft apartment in waterfront community near BWI

Stunning 2-Bedroom loft apartment in waterfront community near BWI is a apartment in Winchester-on-the-Severn, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,294.

From$185/night
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Welcome to our newly built house - Winchester-on-the-Severn, MD

Welcome to our newly built house

Holiday Home, Winchester-on-the-Severn

Welcome to our newly built house is a holiday home in Winchester-on-the-Severn, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Welcome to our newly built house

Welcome to our newly built house is a holiday home in Winchester-on-the-Severn, with pet-friendly 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,158.

From$255/night
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Renovated 3BR | Near Sandy Point Beach - Winchester-on-the-Severn, MD

Renovated 3BR | Near Sandy Point Beach

Holiday Home, Winchester-on-the-Severn

Renovated 3BR · Near Sandy Point Beach is a holiday home in Winchester-on-the-Severn, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Renovated 3BR | Near Sandy Point Beach

Renovated 3BR · Near Sandy Point Beach is a holiday home in Winchester-on-the-Severn, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,125.

From$446/night
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Coastal Modern Retreat | Large Group Getaway on 2 Acres - Winchester-on-the-Severn, MD

Coastal Modern Retreat | Large Group Getaway on 2 Acres

Holiday Home, Winchester-on-the-Severn

Coastal Modern Retreat · Large Group Getaway on 2 Acres is a holiday home in Winchester-on-the-Severn, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Coastal Modern Retreat | Large Group Getaway on 2 Acres

Coastal Modern Retreat · Large Group Getaway on 2 Acres is a holiday home in Winchester-on-the-Severn, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,600.

From$800/night
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Pet-friendly vacation rentals in Winchester-on-the-Severn, MD

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

Glen Burnie Vacation Rental w/ Private Deck! - Winchester-on-the-Severn, MD

Glen Burnie Vacation Rental w/ Private Deck!

Holiday Home, Winchester-on-the-Severn

Glen Burnie Vacation Rental w/ Private Deck! is a holiday home in Winchester-on-the-Severn, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base…

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About Glen Burnie Vacation Rental w/ Private Deck!

Glen Burnie Vacation Rental w/ Private Deck! is a holiday home in Winchester-on-the-Severn, with pet-friendly space, 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 wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,030.

From$181/night
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Londontowne Rancher | 3BR | Near Waterfront - Winchester-on-the-Severn, MD

Londontowne Rancher | 3BR | Near Waterfront

Holiday Home, Winchester-on-the-Severn

Londontowne Rancher · 3BR · Near Waterfront is a holiday home in Winchester-on-the-Severn, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable…

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About Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher · 3BR · Near Waterfront is a holiday home in Winchester-on-the-Severn, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,524.

From$361/night
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Annapolis Home | Fenced Yard | Pool Table | 10 Guests - Winchester-on-the-Severn, MD

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Holiday Home, Winchester-on-the-Severn

Annapolis Home · Fenced Yard · Pool Table · 10 Guests is a holiday home in Winchester-on-the-Severn, with pet-friendly space, pool access, and parking. This stay gives travelers a…

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About Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home · Fenced Yard · Pool Table · 10 Guests is a holiday home in Winchester-on-the-Severn, with pet-friendly space, pool 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,354.

From$479/night
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Liberty Call has multiple gathering spaces, screened-in porch and parking - Winchester-on-the-Severn, MD

Liberty Call has multiple gathering spaces, screened-in porch and parking

Holiday Home, Winchester-on-the-Severn

Liberty Call has multiple gathering spaces, screened-in porch and parking is a holiday home in Winchester-on-the-Severn, with pet-friendly space, parking, and kitchen access. This stay…

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About Liberty Call has multiple gathering spaces, screened-in porch and parking

Liberty Call has multiple gathering spaces, screened-in porch and parking is a holiday home in Winchester-on-the-Severn, 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 $4,120.

From$589/night
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Vacation rentals with a kitchen in Winchester-on-the-Severn, MD

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

Charming 1-bedroom house in wonderful Severn with office, WiFi, fitness room - Winchester-on-the-Severn, MD

Charming 1-bedroom house in wonderful Severn with office, WiFi, fitness room

Holiday Home, Winchester-on-the-Severn

Charming 1-bedroom house in wonderful Severn with office, WiFi, fitness room is a holiday home in Winchester-on-the-Severn, with kitchen access and room for a group. This stay gives…

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About Charming 1-bedroom house in wonderful Severn with office, WiFi, fitness room

Charming 1-bedroom house in wonderful Severn with office, WiFi, fitness room is a holiday home in Winchester-on-the-Severn, 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, hot tub, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $942.

From$135/night
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Glen Burnie Vacation Rental w/ Private Deck! - Winchester-on-the-Severn, MD

Glen Burnie Vacation Rental w/ Private Deck!

Holiday Home, Winchester-on-the-Severn

Glen Burnie Vacation Rental w/ Private Deck! is a holiday home in Winchester-on-the-Severn, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base…

Read more

About Glen Burnie Vacation Rental w/ Private Deck!

Glen Burnie Vacation Rental w/ Private Deck! is a holiday home in Winchester-on-the-Severn, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,816.

From$259/night
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Pasadena, MD close to Annapolis/WDC/Baltimore - Winchester-on-the-Severn, MD

Pasadena, MD close to Annapolis/WDC/Baltimore

Holiday Home, Winchester-on-the-Severn

Pasadena, MD close to Annapolis/WDC/Baltimore is a holiday home in Winchester-on-the-Severn, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Pasadena, MD close to Annapolis/WDC/Baltimore

Pasadena, MD close to Annapolis/WDC/Baltimore is a holiday home in Winchester-on-the-Severn, with 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, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,958.

From$280/night
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Spacious Townhouse in the Heart of Washington D.C. - Winchester-on-the-Severn, MD

Spacious Townhouse in the Heart of Washington D.C.

Holiday Home, Winchester-on-the-Severn

Spacious Townhouse in the Heart of Washington D.C. is a holiday home in Winchester-on-the-Severn, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Spacious Townhouse in the Heart of Washington D.C.

Spacious Townhouse in the Heart of Washington D.C. is a holiday home in Winchester-on-the-Severn, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,989.

From$284/night
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Family-friendly vacation rentals in Winchester-on-the-Severn, MD

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

Spacious 3-Bedroom, 1.5-Bath Home in Central Maryland with Screened Porch & More - Winchester-on-the-Severn, MD

Spacious 3-Bedroom, 1.5-Bath Home in Central Maryland with Screened Porch & More

Holiday Home, Winchester-on-the-Severn

Spacious 3-Bedroom, 1.5-Bath Home in Central Maryland with Screened Porch & More is a holiday home in Winchester-on-the-Severn, with pet-friendly space, kitchen access, and room for a…

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About Spacious 3-Bedroom, 1.5-Bath Home in Central Maryland with Screened Porch & More

Spacious 3-Bedroom, 1.5-Bath Home in Central Maryland with Screened Porch & More is a holiday home in Winchester-on-the-Severn, 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 $1,158.

From$165/night
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Charming 1-bedroom cottage with AC in cozy Harwood - Winchester-on-the-Severn, MD

Charming 1-bedroom cottage with AC in cozy Harwood

Cottage, Winchester-on-the-Severn

Charming 1-bedroom cottage with AC in cozy Harwood is a cottage in Winchester-on-the-Severn, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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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 Winchester-on-the-Severn, 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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Family Home on Mayo Peninsula | Deck | Sleeps 10 - Winchester-on-the-Severn, MD

Family Home on Mayo Peninsula | Deck | Sleeps 10

Holiday Home, Winchester-on-the-Severn

Family Home on Mayo Peninsula · Deck · Sleeps 10 is a holiday home in Winchester-on-the-Severn, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable…

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About Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula · Deck · Sleeps 10 is a holiday home in Winchester-on-the-Severn, with pet-friendly space, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,579.

From$368/night
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Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Navy Sports visitors and the Annapolis Blues games! - Winchester-on-the-Severn, MD

Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Navy Sports visitors and the Annapolis Blues games!

Cottage, Winchester-on-the-Severn

Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Navy Sports visitors and the Annapolis Blues games! is a cottage in Winchester-on-the-Severn, with…

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About Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Navy Sports visitors and the Annapolis Blues games!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Navy Sports visitors and the Annapolis Blues games! is a cottage in Winchester-on-the-Severn, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,792.

From$685/night
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